Hydrazine hydrate (1:1) → HCID 178515479, compound

HRID 466014Notes

Reaction equation

HRID 466014 reaction equation
[C:1]1([C:7]2[C:15]([C:16]#[C:17][C:18]([O:20]C)=O)=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[NH2:23][NH2:24]>C(O)C>[OH:20][C:18]1[NH:24][N:23]=[C:16]([C:15]2[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[N:8][N:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=23)[CH:17]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 15158167HCID 15158167, compound

Product 1

HCID 178515479HCID 178515479, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl 3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)propiolate (1.50 g), hydrazine monohydrate (0.544 g) and ethanol (15 ml) was heated under reflux for 2 hours. Ethanol was evaporated in vacuo. Water (50 ml) was added to the residue and the mixture was acidified with 1N hydrochloric acid. The resultant precipitates were collected by filtration and washed with water. Recrystallization from a mixture of N,N-dimethylformamide and water gave crystals of 3-(5-hydroxypyrazol-3-yl)-2-phenylpyrazolo[1,5-a]pyridine (0.64 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customEthanol was evaporated in vacuo
  4. additionWater (50 ml) was added to the residue
  5. customThe resultant precipitates
  6. filtrationwere collected by filtration
  7. washwashed with water
  8. customRecrystallization
  9. additionfrom a mixture of N,N-dimethylformamide and water

Sources & evidence

ORD record
ord-6d3d30b0e0b54a03af498469e9cf188e
Source dataset
uspto-grants-1992_10
Patent number
US05155114

Reaction notes

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