Acetohydrazide → 7-Bromo-8-chloro-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

HRID 1521636노트

반응식

HRID 1521636 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[NH:8][C:7](=S)[CH2:6][CH2:5]2.[C:14]([NH:17][NH2:18])(=O)[CH3:15]>C(O)CCC>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]1[C:14]([CH3:15])=[N:17][N:18]=[C:7]1[CH2:6][CH2:5]2

참가 물질

4

반응물 2

HCID 14039AcetohydrazideHCID 899617616-bromo-7-chloro-3,4-dihydroquinoline-2(1H)-thione

생성물 1

HCID 709776077-Bromo-8-chloro-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

To a stirred solution of 6-bromo-7-chloro-3,4-dihydroquinoline-2(1H)-thione (110-3; 1.8 g, 0.0065 mol) in n-butanol (80 mL) was added acetic hydrazide (1.2 g, 0.0162 mol). Reaction mass was refluxed for 16 h. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel (60-120 mesh) column chromatography using 0-5% methanol in dichloromethane to afford title compound. 1H NMR (400 MHz, DMSO-d6) δ 7.91 (s, 1H), 7.81 (s, 1H), 2.96 (bs, 4H), 2.66 (s, 3H). MS (M+1): 296.0.

후처리

  1. customReaction mass
  2. temperaturewas refluxed for 16 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel (60-120 mesh) column chromatography

출처 및 근거

ORD 기록
ord-735f18eca1934b21b12c92b242f3a972
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073929B2

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