Ammonium Chloride → 2-Ethoxy-4-aminobenzoic acid

HRID 2105829

반응식

HRID 2105829 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

HCID 101763852-Ethoxy-4-aminobenzoic acid수율 73%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

반응 조건

온도
80 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-3ef8c165b34f44ce9fc441bdc116fc09
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07579368B2

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