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

HRID 1521636ノート

反応式

HRID 1521636 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-735f18eca1934b21b12c92b242f3a972
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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