Check the ignition timing while cranking. Is it off? I'd check the cam timing. If the cam was installed straight up both #6 tappets should be exactly level at #1 TDC compression stroke. Though I'd expect the compression numbers to be lower across the board if the cam chain jumped or cam bolt lose/sheared gear dowel pin and retarded the cam.
Doug

OK, so somehow the distributor was way off. I'm starting to think the timing chain "jumped" as some have suggested. I believe I've got the distributor set back to 0 at top dead center. Should the car start if this is the case? Do I then use my timing light and start adding timing after it starts assuming it does? And if the timing chain did jump, will it likely do it again??

If the timing chain jumped the timing set must be replaced. Jumping means it's either stretched or the gears have gone bad.

Yeah, figured that would be the case. This has been LOTS of learnings for a person with limited mechanical ability. If I take everything off the front of the engine and get to the timing chain cover, do I need to take oil pan off too? I hope not.

no on the pan Q & you'd set the dampener slit to 15 BTDC and move housing till magnet is dead even with the tooth

You have pulled the dist and the dist drive out of the motor. The only way you will know if the timing gears have jumped is to pull the timing cover and look.

Are we sure he didn't just loose ignition for a moment? What are you running for an ignition system? You have a rev limiter, which might suggest maybe an MSD?
I went back and read the 1st post. He heard pinging, then felt loss of power (hit rev limiter, ignition failure, shut down spark, flood plugs with gas (6,000 rpm, no spark). Then it idled at lower then normal rpm (ign came back, but now the plugs are gas fouled). Lost oil pressure (sudden motor shutdown from high rpm, sudden reduction in vehicle speed, worn bearings from NOS?) Then he turned ignition off and hauled it home. No place does he say he checked for spark. He was more concerned about no oil pressure, and pulled the dist & dist drive, then the oil pump and disassembled it.

Oil pump wear consistent with a 40K motor. Lower compression numbers with the rear 2 cylinders consistent with a dual quad street motor probably often running rich. He is showing decent oil pressure with a fresh pump on a cold motor with fresh oil, but that may not be telling the true condition of the rods and the rod bearings with consideration of multiple 6500 rev limiter hits and the addition of nos.

There may or may not be a timing issue, and its something I would be looking at. Baring a timing chain issue, things are adding up to an ignition loss, or partial ignition failure compounded by a worn motor that has seen 40,000 miles of hard use.

It may run if he brings #1 up on compression and gets the dist & dist drive in correctly, adds fresh oil, and new plugs, presuming it has consistent spark. Gene

OK, here's the latest.

I want to answer Gene question in his last post.

I have an MSD pro billet distributor with no more than 300 miles on it connected with an MSD 6AL box. I believe I have the rev limiter set to 6700.

A best friend has been helping me to try and get the issue figured out. The distributor was waaaaay off. It required pulling the pump shaft, gear and resetting it to TDC and then re wiring all of the spark plug wire to the distributor. Once this was done I added some initial advance to the distributor and it started right up, though choppy. I added additional timing and it was starting to run GREAT again when suddenly there was a bad noise from passenger side. Sounds like an exhaust leak or perhaps a lifter knocking. It was not there on first start up. Came at second one when timing was added and it was running better.

Car has better oil pressure than ever with Mopar oil pump and new hardened oil pump shaft.

Current plans are to order new plug wires as one I have on now are cracked at boots and likely arching. Will order new Firecores this week. Do any of you know if there premade ones for a 440 fit a B body well without lots of extra length?

Will also order new Cloyes double roller and try and figure out how to install a replacement. Everything points to the chain jumping of gear tooth breaking as others have suggested.

AND will order new exhaust gaskets for my SuperComp 2" headers hoping it's just an exhaust leak and not a lifter or rod bearing... It's been a long couple of months...for a person with limited mechanic skills...

Any thoughts??? Best way to get to exhaust leak or lifter or rod bearing??

For what it's worth I recall hearing the noise thought no as pronounced in the past and it would go away not long after starting the car once the engine got warmed up.

If it's running it's not the timing chain.
Doug

Doug, several others have offered it the chain could be loose/sloppy or tooth broke on timing gear and jumped. That would seem reasonable to me and explain how the distributor became physical position wrong. How else would you explain it?

The dist was pulled out of the motor, and the dist drive were pulled out of the motor, first post.

Once those were pulled, we have no way of knowing if they were reinstalled in the exact same position when they were reinstalled. Any reference to timing, at that point is a lost cause. It was not checked before it was pulled apart.

If the motor now runs, the timing chain and gears are in the proper place. With a timing chain that has slipped one tooth, the motor will barely run. If it has slipped 2 teeth, it won't start at all. That said, the chain could be stretched, and the gears may be worn, do to the miles on the motor (40,000 mile on a Mopar motor is not a lot of miles, but the amount of abuse the motor has seen does take its tole). That is/was not the cause of your problem. If there were high quality parts used in your motor when it was rebuilt, I would be surprised if the chain or gears are worn very much at all in 40,000 miles. A worn chain/timing gears can cause the ignition timing to retard and could cost you ultimate performance, which would get progressively worse until it jumped a tooth. You can detect a worn timing chain & gears with a timing light watching the timing marks when the motor is idling. The timing mark will move around a few degrees without you doing anything.

The tick when the timing was dialed in does give me some concern, given the compression test numbers. Mopar allowed a 20% difference in compression between the highest cylinder and the lowest cylinder before recommending a rebuild. You are right at that cut. Now that you got the motor running again, I think I would recheck the cylinder compression test and see how closely it matches the first compression test. You might have better numbers now.

The tick could be an exhaust leak, a bad ignition wire, a burnt valve, a cracked piston, a broken crank, a chunk of carbon, a bad lifter, a bad cam lobe, a bent push rod, a damaged rocker, or a few other things.

You still don't know what caused your inimical problem. It was not the timing chain or timing gears, and it was not the oil pump. Back the rev limiter down to about 6200 and stay off the rev limiter! Shift sooner! It will make the motor a lot happier, it will live longer. It will not hurt your performance much, might even be faster! Gene

Thanks Gene for taking the time to provide all this feedback. It's greatly appreciated. I did check the position of the oil pump gear shaft before I pulled it and put the new hardened one in the same position, I also marked the position of the distributor and cap. It's possible they move but Ai was extremely careful the not have that happen.

I feel I used good quality parts when I had the motor built by a professional back in 1993. New stock forged crank, new LY rods, forged TRW 40 over pistons, original max wedge adjustable rockers, deep sump morose oil pan, Cloyes double roller, etc. NOT high grade racing parts, but good street mild strip stuff back then.

I've run 3 bottles of NOS in it over the years. Besides that it's just been run hard on the motor.

Perhaps it was just the rev limiter as you offered. But once it stop running right after I heard the noise it had pretty much no power at all and then just died out about a minute later.

When I get my new spark plug wires I'll fire it back up and check the timing and see if I see the timing move for no reason as you offer. If I do I'm going to try relaxing the timing gear and chain and cross my fingers.

Can anyone tell me how much to torque the crank bolt and the timing chain bolt? I'm looking to chain the timing chain and gear.

Also, is there a good book I can buy that has what to torque all bolts in a 440?

Thanks and Merry Christmas!!

135 on the big crank bolt (clean/dry threads). couldn't find a spec for the cam gear bolt but you cant go wrong with Googling it, need (A) the grade, 3 lines is grade 5 and 6 lines is grade 8 (B) the dia (C) fine or coarse threads & likely someone will chime in before you have to go that far

Straight from my '69 Factory Service Manual: Crankshaft Bolt (Vibration Damper) - 135 ft-lbs.; Camshaft Lock Bolt - 35 ft-lbs.

Hope this works:

...

Wow, you guys are awesome!! Thanks for all the help and responses.

Merry Christmas!!

And my dumb question for the day, do I put my manual transmission in drive to tighten the crank bolt to keep the engine from spinning?? I guess same for the cam bolt?

Oh, and what do you use on the timing chain cover for sealant? RTV blue?

tranny in dr for that. you'll hit 35 before it turns in neutral. I'd brush some permatex #3 aviation gasket cement on a tailor made gasket or spray the same gasket with permatex 99MA "high tack" the thin red spray stuff in the purple can.

OK, here's the latest. we installed new MSD 8.5 wires today, regapped the plugs from 38 to 40 (some were close to 35), tightened the header bolts and a clamp around the header "slip sleeve" with one of the primary tubes, started up the car and no more noise. Shut it off, added some timing and it ran good. Added some more timing and it now idles at 800-900 rpm and has 13 inches of vacuum with no changes made to carbs. This is the MOST vacuum I've gotten in years and the car sounds great and runs smooth.

Still don't know what initially caused the issue. i will say I turned the car off once and turned it back on with no changes and the car idle and vacuum improve (rpm's by 200 and vacuum by almost 3"). I'm guessing it all still points to a sloppy timing chain or messed up gear in some way. We will put a timing light on it tomorrow and see if timing is bouncing around as it was suggested it would do if the timing chain is sloopy.

New question. One is with the new high volume Mopar oil pump installed I'm getting almost 80 psi o foil pressure versus 60 with my previous high volume pump with stock spring. Is this going to cause gaskets to fail or cause other problems for my engine? Do I need to reduce it?