(8-Nitro-quinolin-7-yl)-phenyl-methanol → (8-Amino-quinolin-7-yl)-phenyl-methanol

HRID 513654Notes

Reaction equation

HRID 513654 reaction equation
[N+:1]([C:4]1[C:5]([CH:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[OH:15])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-])=O>[Pd].CCO.CO>[NH2:1][C:4]1[C:5]([CH:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[OH:15])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2

Participants

5

Reactant 1

HCID 68183066(8-Nitro-quinolin-7-yl)-phenyl-methanol2×

Product 1

HCID 68183272(8-Amino-quinolin-7-yl)-phenyl-methanolYield 99.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Palladium on Carbon (10%, 38 mg) was added to a solution of (8-nitro-quinolin-7-yl)-phenyl-methanol (Intermediate 214) (500 mg, 1.78 mmol) in EtOH (20 ml) and the mixture was stirred under an atmosphere of hydrogen for 1.5 h. The mixture was diluted with MeOH (40 ml), filtered through celite and the filtrate was concentrated in vacuo to give the title compound (443 mg, 99%).

Workup

  1. filtrationfiltered through celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-33e20e36a28542969dea9cd28396d563
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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