Formic Acid → 5-Benzyl-6-oxo-5,6-dihydrophenanthridine-2-carboxaldehyde

HRID 1811423Notes

Reaction equation

HRID 1811423 reaction equation
[CH2:1]([N:8]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]2[CH:13]=[C:12]([C:23]#N)[CH:11]=[CH:10][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)=[O:26]>[Ni]>[CH2:1]([N:8]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]2[CH:13]=[C:12]([CH:23]=[O:26])[CH:11]=[CH:10][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 665968095-Benzyl-6-oxo-5,6-dihydrophenanthridine-2-carbonitrile

Product 1

HCID 862337835-Benzyl-6-oxo-5,6-dihydrophenanthridine-2-carboxaldehydeYield 80%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

5-Benzyl-6-oxo-5,6-dihydrophenanthridine-2-carbonitrile (1.24 g) and Raney nickel (0.8 g) were suspended in 75% formic acid (25 ml). The suspension was heated under reflux for 1 hour and 40 minutes, and filtered while hot. The filtrate was concentrated and purified by silica gel chromatography (methylene chloride:methanol=50:1) to thereby obtain 1.08 g (yield: 80%) of the title compound as a colorless crystals.

Workup

  1. temperatureThe suspension was heated
  2. temperatureunder reflux for 1 hour and 40 minutes
  3. filtrationfiltered while hot
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel chromatography (methylene chloride:methanol=50:1)

Sources & evidence

ORD record
ord-320d901322fc43459cff173567946ca8
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

Loading…