3-Aminocyclohex-2-en-1-one → 2-methyl-7,8-dihydro-6H-quinolin-5-one

HRID 1973673노트

반응식

HRID 1973673 반응식
[NH2:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1.CO[CH:11]=[CH:12][C:13](=O)[CH3:14]>>[CH3:14][C:13]1[CH:12]=[CH:11][C:3]2[C:4](=[O:8])[CH2:5][CH2:6][CH2:7][C:2]=2[N:1]=1

참가 물질

3

반응물 2

HCID 788923-Aminocyclohex-2-en-1-oneHCID 942973-Buten-2-one, 4-methoxy-

생성물 1

HCID 103295782-methyl-7,8-dihydro-6H-quinolin-5-one수율 72%

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온도
120 °C

실험 절차

A mixture of 3-aminocyclohex-2-enone (22 g., 0.2 mol.) and 4-methoxybut-3-en-2-one (20.0 g., 0.2 mol), in an apparatus equipped for downward distillation, was heated in an oil bath at 120° C until the theoretical amount of distillate had been collected (13 ml.). The cooled residue was dissolved in 2N HCl (50 ml.) and extracted with ethyl acetate (3 × 50 ml.) and the combined extracts discarded. The aqueous solution was adjusted to pH 9.0 with sodium carbonate and extracted with chloroform (3 × 50 ml.). The combined extracts were dried (MgSO4) and the solvent removed in vacuo and the residual oil distilled to give the title compound (22.5 g., 72%) b.p. 72°-6°/0.1 mm Hg. The free base was dissolved in ether and treated with an excess of ethereal hydrogen chloride. The resultant solid was isolated and recrystallised from isopropanol to give the hydrochloride of the title compound as colourless needles m.p. 225° C. (Found: C, 60.9; H, 6.3; N, 6.99. C10H11NO.HCl requires: C, 60.7; H, 6.1; N, 7.1%).

후처리

  1. customin an apparatus equipped for downward distillation
  2. customhad been collected (13 ml.)
  3. dissolutionThe cooled residue was dissolved in 2N HCl (50 ml.)
  4. extractionextracted with ethyl acetate (3 × 50 ml.)
  5. extractionextracted with chloroform (3 × 50 ml.)
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. customthe solvent removed in vacuo
  8. distillationthe residual oil distilled

출처 및 근거

ORD 기록
ord-942ada9f90b74802b30413e726f69e70
출처 데이터셋
uspto-grants-1976_12
특허 번호
US03998831

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