3-Hydroxy-4'-methoxy-2-nitrobenzanilide → 2-Amino-3-hydroxy-4'-methoxybenzanilide

HRID 478168Notes

Reaction equation

HRID 478168 reaction equation
[OH:1][C:2]1[C:3]([N+:19]([O-])=O)=[C:4]([CH:16]=[CH:17][CH:18]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)=[O:6].[H][H]>CO.[C].[Pd]>[NH2:19][C:3]1[C:2]([OH:1])=[CH:18][CH:17]=[CH:16][C:4]=1[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=1)=[O:6]

Participants

5

Reactant 2

HCID 180011313-Hydroxy-4'-methoxy-2-nitrobenzanilideHCID 178418361HCID 178418361, compound

Product 1

HCID 180011072-Amino-3-hydroxy-4'-methoxybenzanilideYield 93.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

3-Hydroxy-4′-methoxy-2-nitrobenzanilide (1.15 g) was suspended in 50 ml of methanol, 300 mg of 10% palladium-carbon powder were added and the mixture was stirred in a hydrogen atmosphere at room temperature for 1 hour. The reaction solution was filtered through Celite and washed with methanol and the filtrate was concentrated in vacuo to give 966 mg of 2-amino-3-hydroxy-4′-methoxybenzanilide.

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. washwashed with methanol
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7d3918c3648643ac998fd4ea29152368
Source dataset
uspto-grants-2003_11
Patent number
US06642224B1

Reaction notes

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