Ammonium Chloride → 2-Ethoxy-4-aminobenzoic acid

HRID 2105829

Reaction equation

HRID 2105829 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])[CH3:2].[Cl-].[NH4+]>C(O)C.[Fe]>[NH2:13][C:11]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:3][CH2:1][CH3:2])[CH:12]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 27363472-Ethoxy-4-nitrobenzoic acid

Product 1

HCID 101763852-Ethoxy-4-aminobenzoic acidYield 73%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Iron (16.19 g, 290 mmol) was added to a slurry mixture of 2-ethoxy-4-nitrobenzoic acid (24.00 g, 114 mmol) in ethanol (200 mL) and saturated aqueous solution of ammonium chloride (120 mL). The mixture was stirred at 80° C. for 2 h. The reaction mixture was cooled to room temperature and filtered through Celite. It was rinsed with methylene chloride and the combined filtrate diluted with water and extracted with methylene chloride and dried over anhydrous sodium sulfate. Evaporation of the solvent and chromatography of the brown residue over silica gel using 1-5% methanol in methylene chloride produced 4-amino-2-ethoxybenzoic acid as a yellow solid (14.94 g, 73%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through Celite
  3. washIt was rinsed with methylene chloride
  4. additionthe combined filtrate diluted with water
  5. extractionextracted with methylene chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customEvaporation of the solvent and chromatography of the brown residue over silica gel using 1-5% methanol in methylene chloride

Sources & evidence

ORD record
ord-3ef8c165b34f44ce9fc441bdc116fc09
Source dataset
uspto-grants-2009_08
Patent number
US07579368B2

Linked notes

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