3-Phenylquinoline-5-carbonitrile → 3-Phenyl-5-hydroxymethylquinoline

HRID 266224Notes

Reaction equation

HRID 266224 reaction equation
C1(C2C=NC3C=CC=C(C#N)C=3C=2)C=CC=CC=1.[C:19]1([C:25]2[CH:26]=[N:27][C:28]3[CH:29]=[CH:30][CH:31]=[C:32]([CH:35]=[O:36])[C:33]=3[CH:34]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)=O.[Ni]>[C:19]1([C:25]2[CH:26]=[N:27][C:28]3[C:33]([CH:34]=2)=[C:32]([CH2:35][OH:36])[CH:31]=[CH:30][CH:29]=3)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 97946013-Phenylquinoline-5-carbonitrileHCID 151703323-Phenylquinoline-5-carbaldehyde

Product 1

HCID 190332423-Phenyl-5-hydroxymethylquinoline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 284Formic AcidSolvent

Conditions

Temperature
80 °C

Procedure

23 g (0.1 mol) of 3-phenylquinoline-5-carbonitrile (substance from Example 4) are admixed in 150 ml of formic acid with 10 g of Raney nickel. The mixture is stirred for about 5 hours at about 80° C. The slow formation of 3-phenylquinoline-5-carbaldehyde is observed by means of HPLC. In addition, 3-phenyl-5-hydroxymethylquinoline is formed as overreduced product. For the work-up, 300 ml of H2O are stirred in and the mixture is optionally extracted with 200 ml of methylene chloride. The methylene chloride phase is subsequently stirred at 40° C. (reflux) for 2 hours with 10 g of manganese dioxide. After filtration, the solution is evaporated and the residue is recrystallized from isopropanol.

Sources & evidence

ORD record
ord-6a3a62b38270439298ccd4a951e2a739
Source dataset
uspto-grants-1997_07
Patent number
US05650514

Reaction notes

Loading…