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

HRID 1521636Notes

Reaction equation

HRID 1521636 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-735f18eca1934b21b12c92b242f3a972
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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