Ethanol → 4-Amino-3-ethoxybenzoic acid

HRID 2234441Notes

Reaction equation

HRID 2234441 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N+:13]([O-])=O)[C:7]([OH:9])=[O:8])[CH3:2].C(O)C>[Pd].CN(C=O)C>[NH2:13][C:12]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[O:3][CH2:1][CH3:2]

Participants

5

Reactant 2

HCID 702EthanolHCID 223975093-Ethoxy-4-nitrobenzoic acid2×

Product 1

HCID 223974484-Amino-3-ethoxybenzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-ethoxy-4-nitrobenzoic acid (Intermediate 165; 1.0 g, 4.74 mmol) ethanol:DMF (50 mL:5 mL) over 5% Pd/C catalyst (100 mg) was hydrogenated with stirring at ambient temperature for 4 hours. The mixture was filtered and the catalyst washed with ethanol and the solvent evaporated and the residue that on trituration with diethyl ether yielded the title compound as an off white solid (688 mg, 81%)

Workup

  1. filtrationThe mixture was filtered
  2. washthe catalyst washed with ethanol
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-13d0c4503e1442a4b5105546faa36205
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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