4-Nitro-o-toluic acid → 4-amino-2-methylbenzoic acid

HRID 1518628Notes

Reaction equation

HRID 1518628 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]>CO.[C].[Pd]>[NH2:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([CH3:1])[CH:10]=1

Participants

4

Reactant 1

HCID 747904-Nitro-o-toluic acid

Product 1

HCID 2416324-amino-2-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

2-Methyl-4-nitrobenzoic acid (741 g, 5 mmol) was dissolved in methanol (20 mL), 10% palladium-carbon (100 mg) was added, and the mixture was stirred under a hydrogen atmosphere at room temperature for 16 hours. The reaction solution was filtered through celite and, thereafter, the filtrate was concentrated under reduced pressure to obtain 4-amino-2-methylbenzoic acid as a crude material. In accordance with Reference Example 23 and Reference Example 14, from 4-amino-2-methylbenzoic acid obtained, there was obtained 4-[(tert-butyldimethylsilanoyloxy)methyl]-3-methylaniline (0.33 g).

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-dd0583f9129a47ed967969e457feb56b
Source dataset
uspto-grants-2015_07
Patent number
US09072734B2

Reaction notes

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