Hydrazine hydrate (1:1) → 3-amino-5-(2-chlorophenyl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one

HRID 1526347Notes

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[Cl: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[Cl:14])[CH:6]=[CH:7][C:2]=2[NH:20][N:19]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 4-chloro-1-(2-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile obtained in Step D (891 mg) in ethanol (6.72 mL) was added hydrazine monohydrate (252 mg) at room temperature. The reaction mixture was heated at 90° C. for 5 hr, 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 dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (854 mg).

Workup

temperaturecooled to room temperature
concentrationThe reaction mixture was concentrated under reduced pressure, to the residue
additionwas added water
extractionthe mixture was extracted with ethyl acetate
dry with materialThe extract was dried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-b7cba63eb3454c0293200933c483dbaf
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085578B2

Reaction notes

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