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

HRID 1521653Notes

Reaction equation

HRID 1521653 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[NH:8][C:7](=S)[CH2:6][CH2:5][C:4]=2[C:3]=1[C:13]#[N:14].[C:15]([NH:18][NH2:19])(=O)[CH3:16]>C(O)CCC>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]3[C:15]([CH3:16])=[N:18][N:19]=[C:7]3[CH2:6][CH2:5][C:4]=2[C:3]=1[C:13]#[N:14]

Participants

4

Reactant 2

HCID 14039AcetohydrazideHCID 891560546-Bromo-2-thioxo-1,2,3,4-tetrahydroquinoline-5-carbonitrile

Product 1

HCID 709778147-Bromo-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 6-bromo-2-thioxo-1,2,3,4-tetrahydroquinoline-5-carbonitrile (145-3; 0.5 g, 0.00188 mol) in n-butanol (10 mL) was added acetic hydrazide (0.35 g, 0.0047 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): 289.

Workup

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

Sources & evidence

ORD record
ord-f9170e89447b41ae95cf9e06308ca322
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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