Methyl 3,5-dimethyl-4-nitrobenzoate → Benzoic acid, 4-amino-3,5-dimethyl-, methyl ester

HRID 1166999Notes

Reaction equation

HRID 1166999 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([N+:12]([O-])=O)=[C:7]([CH3:15])[CH:6]=1)([O:3][CH3:4])=[O:2]>C(OCC)(=O)C.[Pd]>[C:1]([C:5]1[CH:6]=[C:7]([CH3:15])[C:8]([NH2:12])=[C:9]([CH3:11])[CH:10]=1)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 1

HCID 22998442Methyl 3,5-dimethyl-4-nitrobenzoate

Product 1

HCID 11030398Benzoic acid, 4-amino-3,5-dimethyl-, methyl esterYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-Carbomethoxy-2,6-dimethylnitrobenzene (2 g, 9.5 mmol) was dissolved in in ethyl acetate (20 ml) and subjected to catalytic hydrogenation using 10% palladium on carbon (300 mg) at 55 psi for 30 min. The catalyst was filtered and solvent removed to give 4-carbomethoxy-2,6-dimethylaniline as a solid (1.7 g, 100% yield).

Workup

  1. customfor 30 min
  2. filtrationThe catalyst was filtered
  3. customsolvent removed

Sources & evidence

ORD record
ord-2ed7af2ad2e348e6baafe34133dee14a
Source dataset
uspto-grants-2003_09
Patent number
US06613804B2

Reaction notes

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