3-Methyl-2-nitrobenzoic acid → 2-Amino-3-methylbenzoic acid

HRID 1583247Notes

Reaction equation

HRID 1583247 reaction equation
[CH3:1][C:2]1[C:3]([N+:11]([O-])=O)=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[H][H]>C(O)C.[Pd]>[NH2:11][C:3]1[C:2]([CH3:1])=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 215753-Methyl-2-nitrobenzoic acidHCID 178418361HCID 178418361, compound2×

Product 1

HCID 781012-Amino-3-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-methyl-2-nitrobenzoic acid (7 g) in ethanol (250 ml) was reduced with hydrogen gas at 2 psi over 5% palladium/carbon (0.7 g) catalyst. After hydrogen uptake ceased, the mixture was filtered and solvent removed by a rotary evaporator to give a white solid. Purification was by recrystallization from ethyl ether-hexane, m.p. ca. 170°-173° C.

Workup

  1. filtrationthe mixture was filtered
  2. customsolvent removed by a rotary evaporator
  3. customto give a white solid
  4. customPurification
  5. customwas by recrystallization from ethyl ether-hexane, m.p. ca. 170°-173° C.

Sources & evidence

ORD record
ord-345efaaa2d84485889955ab4adc815de
Source dataset
uspto-grants-1985_11
Patent number
US04551279

Reaction notes

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