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

HRID 1521621Notes

Reaction equation

HRID 1521621 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c9729ef9400e45d68eec503bb955bbb0
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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