Water → HCID 117770200, compound

HRID 1526296Notes

Reaction equation

HRID 1526296 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[C:4](=O)[C:3]=1[C:22]#[N:23].[OH2:24].[NH2:25][NH2:26].O>C(O)C>[NH2:23][C:22]1[C:3]2[C:4](=[O:24])[N:5]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH3:20])[CH:6]=[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:2]=2[NH:26][N:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 117769806HCID 117769806, compound

Product 1

HCID 117770200HCID 117770200, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-chloro-1-(2-methylphenyl)-2-oxo-5-phenyl-1,2-dihydropyridine-3-carbonitrile obtained in Step B (255 mg) in ethanol (1.6 mL) was added hydrazine monohydrate (59.7 mg) at room temperature. The reaction mixture was heated at 70° C. for 2 hr, and cooled to room temperature, water was added thereto, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by thin layer silica gel chromatography (methanol/dichloromethane) to give the title compound (67.0 mg).

Workup

  1. temperaturecooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by thin layer silica gel chromatography (methanol/dichloromethane)

Sources & evidence

ORD record
ord-59084da679154b9c93769610f859d969
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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