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

HRID 1521621ノート

反応式

HRID 1521621 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 2631-Butanol溶媒HCID 962Water溶媒

反応条件

温度
140 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c9729ef9400e45d68eec503bb955bbb0
出典データセット
uspto-grants-2015_07
特許番号
US09073929B2

反応ノート

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