Formic Acid → 6-Methoxy-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbonitrile

HRID 2358305Notes

Reaction equation

HRID 2358305 reaction equation
C([N:4]1[C:13]([C:14]#[N:15])=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:22][CH3:23])[CH:10]=2)[C:5]1=[O:24])C=C.C(N(CC)CC)C.C(O)=O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:23][O:22][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[C:5](=[O:24])[NH:4][C:13]([C:14]#[N:15])=[C:12]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 111745252-Allyl-6-methoxy-1-oxo-4-phenyl-1.2-dihydroisoquinoline-3-carbonitrile

Product 1

HCID 112428516-Methoxy-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Allyl ether 88 (0.5 g, 1.6 mmol) was dissolved in dioxane (10 mL). Triethylamine (0.55 mL, 4 mmol) and formic acid (0.12 mL, 3.2 mmol) were added and the reaction mixture purged with argon. Pd(PPh3)4 (91 mg, 0.08 mmol) was added and the mixture heat to 100 C under a stream of Ar for 1.5 h. A precipitate formed upon cooling. It was isolated by filtration to give 97 as a white solid.

Workup

  1. customthe reaction mixture purged with argon
  2. temperaturethe mixture heat to 100 C under a stream of Ar for 1.5 h
  3. customA precipitate formed
  4. temperatureupon cooling
  5. customIt was isolated by filtration

Sources & evidence

ORD record
ord-7dc60846fc7144db8c8e7af3c71c3ed3
Source dataset
uspto-grants-2010_07
Patent number
US07763614B2

Reaction notes

Loading…