Hydrazine hydrate (1:1) → 6-chloro-4-methyl-1H-pyrazolo[4,3-c]pyridin-3(2H)-one

HRID 588083Notes

Reaction equation

HRID 588083 reaction equation
Cl[C:2]1[C:7]([C:8](OCC)=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]([Cl:14])[CH:3]=1.O.[NH2:16][NH2:17]>C(O)C.O>[Cl:14][C:4]1[N:5]=[C:6]([CH3:13])[C:7]2[C:8](=[O:9])[NH:16][NH:17][C:2]=2[CH:3]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 2786748Ethyl 4,6-dichloro-2-methylnicotinate

Product 1

HCID 826552466-chloro-4-methyl-1H-pyrazolo[4,3-c]pyridin-3(2H)-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 4,6-dichloro-2-methylnicotinate (5.00 g, 21.36 mmol) and hydrazine monohydrate (2.1 mL, 43.3 mmol) in ethanol (22 mL) was heated to 80° C. and stirred for 17.5 h. The reaction was cooled to room temperature, diluted with water, filtered, rinsed with water, and dried under vacuum to provide 6-chloro-4-methyl-1H-pyrazolo[4,3-c]pyridin-3(2H)-one, which was carried onto the next step without further purification. MS ESI calc'd. for C7H6ClN3O [M+1]+ 184. found 184.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered
  3. washrinsed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-b2c3e1f54fb14e66aafa62ede51ef4f0
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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