Formic Acid → 1-(5-Chloro-2-methoxyphenyl)ethanamine

HRID 1910552

반응식

HRID 1910552 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([C:8](=O)[CH3:9])[CH:7]=1.C(O)=O.C([NH2:18])=O>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:8]([NH2:18])[CH3:9])[CH:7]=1

참가 물질

5

반응물 3

HCID 284Formic AcidHCID 713FormamideHCID 2404341-(5-Chloro-2-methoxyphenyl)ethanone

생성물 1

HCID 45381491-(5-Chloro-2-methoxyphenyl)ethanamine

시약·촉매·용매 1

HCID 962Water용매

실험 절차

1-(5-Chloro-2-methoxyphenyl)ethanone (6.7 g, 36.3 mmol) and formic acid (1.74 g, 27.7 mmol) were heated in formamide (10 mL) at 170° C. for 20 h. The mixture was cooled to room temperature, diluted with water and extracted with benzene. After removal of benzene by rotary evaporation the crude mixture was heated under reflux conditions in 3M HCl for 30 h. After cooling, the reaction was added to ether and extracted. The aqueous layer was basified with NaOH to pH 9 and extracted with dichloromethane. The dichloromethane was evaporated to collect the title compound (2.7 g, 40%). 1H NMR (400 MHz, CDCl3): δ 7.39 (d, 1H), 7.26 (q, 1H), 6.81 (d, 1H), 4.62 (m, 1H), 3.84 (s, 3H), 1.69 (d, 3H).

후처리

  1. extractionextracted with benzene
  2. customAfter removal of benzene
  3. customby rotary evaporation the crude mixture
  4. temperaturewas heated under reflux conditions in 3M HCl for 30 h
  5. temperatureAfter cooling
  6. additionthe reaction was added to ether
  7. extractionextracted
  8. extractionextracted with dichloromethane
  9. customThe dichloromethane was evaporated
  10. customto collect the title compound (2.7 g, 40%)

출처 및 근거

ORD 기록
ord-54abd3a22d8e4366a54641f4650ffa43
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604021B2

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