Water → 3-amino-7-bromo-5-(2-chlorophenyl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one

HRID 1526349Notes

Reaction equation

HRID 1526349 reaction equation
[Br:1][C:2]1[C:3](Cl)=[C:4]([C:16]#[N:17])[C:5](=O)[N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[CH:7]=1.[OH2:19].[NH2:20][NH2:21].O>C(O)C>[NH2:17][C:16]1[C:4]2[C:5](=[O:19])[N:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[Cl:14])[CH:7]=[C:2]([Br:1])[C:3]=2[NH:21][N:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 117770380HCID 117770380, compound

Product 1

HCID 1177700033-amino-7-bromo-5-(2-chlorophenyl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-oneYield 81.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 5-bromo-4-chloro-1-(2-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile obtained in Step A (20.9 g) in ethanol (122 mL) was added hydrazine monohydrate (6.08 g) at room temperature. The reaction mixture was heated at 70° C. for 2 hr. The reaction mixture was cooled to room temperature, and poured into water. The resulting solid was collected by filtration, and washed with water to give the title compound (16.9 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-80019d7dd27d498080857134c172226a
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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