Ethyl 3,5-dimethyl-4-nitrobenzoate → Benzoic acid, 4-amino-3,5-dimethyl-, ethyl ester

HRID 1282060Notes

Reaction equation

HRID 1282060 reaction equation
[N+:1]([C:4]1[C:9]([CH3:10])=[CH:8][C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][C:5]=1[CH3:16])([O-])=O>C(OCC)(=O)C.[C].[Pd]>[NH2:1][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][C:5]=1[CH3:16]

Participants

4

Reactant 1

HCID 18423120Ethyl 3,5-dimethyl-4-nitrobenzoate

Product 1

HCID 201013Benzoic acid, 4-amino-3,5-dimethyl-, ethyl esterYield 99%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 4-nitromesitylenate (7.7 g) in ethyl acetate (300 ml) was added 10% palladium-carbon (3 g) and the mixture was stirred for 3.5 hr under a hydrogen atmosphere. The catalyst was filtered off from the reaction mixture and the filtrate was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to give the title compound (6.6 g) as pale-brown crystals.

Workup

  1. filtrationThe catalyst was filtered off from the reaction mixture
  2. washthe filtrate was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-4f57684774f445b1acccf9eafa641a49
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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