Chloroform → 8-(3-Amino-2,6-dimethylbenzyloxy)-2-methylquinoline

HRID 613605노트

반응식

HRID 613605 반응식
[CH3:1][C:2]1[C:20]([N+:21]([O-])=O)=[CH:19][CH:18]=[C:17]([CH3:24])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2.O.NN.C(Cl)(Cl)Cl>CO>[NH2:21][C:20]1[C:2]([CH3:1])=[C:3]([C:17]([CH3:24])=[CH:18][CH:19]=1)[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2

참가 물질

5

반응물 3

HCID 6212ChloroformHCID 24654Hydrazine hydrate (1:1)HCID 183218528-(2,6-Dimethyl-3-nitrobenzyloxy)-2-methylquinoline

생성물 1

HCID 183218048-(3-Amino-2,6-dimethylbenzyloxy)-2-methylquinoline수율 78.7%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

To a suspension of 8-(2,6-dimethyl-3-nitrobenzyloxy)-2-methylquinoline (2.34 g), ferric chloride (70.6 mg) and carbon (70.6 mg) in methanol (35 ml) was added hydrazine monohydrate (1.09 g) at 65° C., and the mixture was refluxed for 2 hours. Methanol (20 ml) was added thereto, and the mixture was refluxed for 1 hour. After cooling chloroform was added thereto, and the resulting precipitates were filtered off. The filtrate was concentrated and the residue was dissolved in chloroform. The solution was washed with saturated sodium bicarbonate solution, water and brine, dried over magnesium sulfate and concentrated. The residue was crystallized with ethyl acetate to give 8-(3-amino-2,6-dimethylbenzyloxy)-2-methylquinoline (1.67 g) as a pale brown crystal.

후처리

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperaturethe mixture was refluxed for 1 hour
  3. additionwas added
  4. customthe resulting precipitates
  5. filtrationwere filtered off
  6. concentrationThe filtrate was concentrated
  7. dissolutionthe residue was dissolved in chloroform
  8. washThe solution was washed with saturated sodium bicarbonate solution, water and brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated
  11. customThe residue was crystallized with ethyl acetate

출처 및 근거

ORD 기록
ord-803cccb73a9e4c939fd0dfc71a9eb9d8
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06008229

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