3-(benzyloxy)-N-(2-fluoro-5-methylphenyl)benzamide → N-(2-fluoro-5-methylphenyl)-3-hydroxybenzamide

HRID 525833Notes

Reaction equation

HRID 525833 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=1)[C:12]([NH:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=1[F:22])=[O:13])C1C=CC=CC=1>CO>[F:22][C:16]1[CH:17]=[CH:18][C:19]([CH3:21])=[CH:20][C:15]=1[NH:14][C:12](=[O:13])[C:11]1[CH:23]=[CH:24][CH:25]=[C:9]([OH:8])[CH:10]=1

Participants

3

Reactant 1

HCID 429677573-(benzyloxy)-N-(2-fluoro-5-methylphenyl)benzamide

Product 1

HCID 28879615N-(2-fluoro-5-methylphenyl)-3-hydroxybenzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(benzyloxy)-N-(2-fluoro-5-methylphenyl)benzamide (1.5 g, 4.48 mmol from Step 1) in 20 ml of MeOH containing 10% Pd/C (150 mg) was stirred under a hydrogen balloon at room temperature for 2 hours. The catalyst was removed by filtration. The filtrate solution was evaporated to dryness under reduced pressure to give N-(2-fluoro-5-methylphenyl)-3-hydroxybenzamide as light-beige solid. Yield: 1.1 g, 100%.

Workup

  1. customThe catalyst was removed by filtration
  2. customThe filtrate solution was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-0e96694e2b3c4e85b807c9d11e6357a3
Source dataset
uspto-grants-2016_05
Patent number
US09340555B2

Reaction notes

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