Ammonium Chloride → 6-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-one

HRID 723892노트

반응식

HRID 723892 반응식
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-])=O)=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1=[O:15].[Cl-].[NH4+]>CCO.O.[Fe]>[NH2:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[N:2]([CH3:1])[C:3](=[O:15])[CH2:4][CH2:5]2

참가 물질

6

반응물 2

HCID 25517Ammonium ChlorideHCID 218779431-methyl-6-nitro-3,4-dihydroquinolin-2(1H)-one

생성물 1

HCID 218777566-Amino-1-methyl-3,4-dihydroquinolin-2(1H)-one수율 97%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a stirred suspension of 1-methyl-6-nitro-3,4-dihydro-1H-quinolin-2-one (Step 2, 1.04 g, 5.05 mmol) in EtOH (10 mL) and water (5 mL) is added ammonium chloride (2.70 g, 10.0 equiv.). To this mixture is added iron powder (0.85 g, 3.0 equiv.) in 3 portions. The resulting mixture is heated at reflux for 2 h and then is cooled to room temperature. The resulting mixture is filtered through celite and the filtrate is further diluted with water (100 mL). The filtrate is extracted with ethyl acetate (2×50 mL) and washed with saline (100 mL). The organic layers are combined, dried over MgSO4 and concentrated under reduced pressure to yield the title compound as a yellow solid (0.86 g, 97%), MS (m/z): 177.5 [M+H]+.

후처리

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux for 2 h
  3. filtrationThe resulting mixture is filtered through celite
  4. additionthe filtrate is further diluted with water (100 mL)
  5. extractionThe filtrate is extracted with ethyl acetate (2×50 mL)
  6. washwashed with saline (100 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e987e9f1928847e1b6720bb8f8bafe76
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141588B2

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