2-Methyl-5-nitrobenzoic acid → 5-Amino-2-methylbenzoic acid

HRID 524319Notes

Reaction equation

HRID 524319 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]>C(O)C.[Pd]>[NH2:11][C:8]1[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

4

Reactant 1

HCID 5196832-Methyl-5-nitrobenzoic acid

Product 1

HCID 103746145-Amino-2-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5.24 g of 2-methyl-5-nitrobenzoic acid are dissolved in 250 ml of ethanol, 0.5 g palladium on charcoal (5%) are added, and the reaction mixture is stirred under an atmosphere of hydrogen at RT over night, until the reaction is completed according to TLC analysis. The mixture is filtered over a plug of celite, and the solvent is removed under reduced pressure resulting in the crude 5-amino-2-methylbenzoic acid, which is used for the next step without further purification.

Workup

  1. filtrationThe mixture is filtered over a plug of celite
  2. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-32111b1c3dbc4432bbfa1b1411f1ef2e
Source dataset
uspto-grants-2016_05
Patent number
US09340522B2

Reaction notes

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