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

HRID 1521621노트

반응식

HRID 1521621 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=S)[CH2:6][CH2:5]2.[C:13]([NH:16][NH2:17])(=O)[CH3:14]>C(O)CCC.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[C:13]([CH3:14])=[N:16][N:17]=[C:7]1[CH2:6][CH2:5]2

참가 물질

5

반응물 2

HCID 14039AcetohydrazideHCID 573709906-Bromo-3,4-dihydroquinoline-2(1H)-thione

생성물 1

HCID 709778947-Bromo-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

시약·촉매·용매 2

HCID 2631-Butanol용매HCID 962Water용매

반응 조건

온도
140 °C

실험 절차

To a stirred solution of 6-bromo-3,4-dihydroquinoline-2(1H)-thione (74-4; 1.0 g, 0.004 mol) in n-butanol (20 mL) was added acetic hydrazide (1.19 g, 0.016 mol) at room temperature. Reaction mass was allowed to stir at 140° C. for 5 h. The reaction mixture was cooled to room temperature, diluted with water (50 mL) and extracted with ethyl acetate (3×25 mL). The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under vacuum to afford the crude compound. Crude compound was purified by silica gel column chromatography to obtain title compound. MS (M+2): 266.0.

후처리

  1. customReaction mass
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionextracted with ethyl acetate (3×25 mL)
  4. washThe combined organic layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under vacuum
  7. customto afford the crude compound
  8. customCrude compound was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-c9729ef9400e45d68eec503bb955bbb0
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073929B2

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