Hydrazinecarboxaldehyde → HCID 21543699, compound

HRID 1521620Notes

Reaction equation

HRID 1521620 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.[CH:13]([NH:15][NH2:16])=O>C(O)CCC.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:13]=[N:15][N:16]=[C:7]1[CH2:6][CH2:5]2

Participants

5

Reactant 2

HCID 12229HydrazinecarboxaldehydeHCID 573709906-Bromo-3,4-dihydroquinoline-2(1H)-thione

Product 1

HCID 21543699HCID 21543699, compound

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; 0.17 g, 0.0007 mol) in n-butanol (2 mL) was added formic hydrazide (0.105 g, 0.0017 mol) at room temperature. Reaction mass was allowed to stir at 140° C. for 1 h under microwave irradiation conditions. The reaction mixture was cooled to room temperature, diluted with water (10 mL) and extracted with ethyl acetate (2×10 mL). The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under vacuum to afford title compound. MS (M+3): 252.2.

Workup

  1. customReaction mass
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionextracted with ethyl acetate (2×10 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

Sources & evidence

ORD record
ord-0761eab62e0443078756c87e328a7434
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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