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

HRID 1738574Notes

Reaction equation

HRID 1738574 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 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-000158606fa44431b32a1c55def98615
Source dataset
uspto-grants-1999_10
Patent number
US05962490

Reaction notes

Loading…