Hydrazine hydrate (1:1) → HCID 117770638, compound

HRID 1526292Notes

Reaction equation

HRID 1526292 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:14])[C:4](=O)[C:3]=1[C:16]#[N:17].[OH2:18].[NH2:19][NH2:20]>C(O)C>[NH2:17][C:16]1[C:3]2[C:4](=[O:18])[N:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH3:14])[CH:6]=[CH:7][C:2]=2[NH:20][N:19]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 117770476HCID 117770476, compound

Product 1

HCID 117770638HCID 117770638, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-chloro-1-(2-methylphenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile obtained in Step D (3.15 g) in ethanol (10 mL) was added hydrazine monohydrate (1.58 mL) at room temperature. The reaction mixture was heated overnight at 90° C., and cooled to room temperature. The reaction mixture was concentrated under reduced pressure, to the residue was added water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (3.14 g).

Workup

  1. temperaturecooled to room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure, to the residue
  3. additionwas added water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-64f94cffb29f4dfcb69b5d702f807ebf
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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