Acetohydrazide → 7-Bromo-6-chloro-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

HRID 1521648Notes

Reaction equation

HRID 1521648 reaction equation
[Br:1][C:2]1[C:3]([Cl:13])=[C:4]2[C:9](=[CH:10][CH:11]=1)[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[C:3]([Cl:13])=[C:4]2[C:9](=[CH:10][CH:11]=1)[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 899617066-bromo-5-chloro-3,4-dihydroquinoline-2(1H)-thione

Product 1

HCID 709781657-Bromo-6-chloro-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 6-bromo-5-chloro-3,4-dihydroquinoline-2(1H)-thione (143-6; 0.3 g, 0.0012 mol) in n-butanol (10 mL) was added acetic hydrazide (0.2 g, 0.00213 mol). Reaction mass was heated at 120° C. for 16 h. The reaction mixture was concentrated and directly purified by silica gel column chromatography to obtain title compound. MS (M+1): 298.0.

Workup

  1. customReaction mass
  2. concentrationThe reaction mixture was concentrated
  3. customdirectly purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d32067c7a7654c89a5f44ef879dbf804
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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