Hydrazine hydrate (1:1) → 3-Amino-5-(4-methoxyphenyl)pyrazole

HRID 1695206

Reaction equation

HRID 1695206 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][C:11]#[N:12])=[CH:5][CH:4]=1.O.[NH2:15][NH2:16]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:16][N:15]=[C:11]([NH2:12])[CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 2333984-Methoxybenzoylacetonitrile

Product 1

HCID 27564693-Amino-5-(4-methoxyphenyl)pyrazoleYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 3-(4-methoxyphenyl)-3-oxopropanenitrile in ethanol was heated to 60° C. Hydrazine hydrate was added dropwise over a minimum of 30 min at 60° C. The resulting solution was held at 60° C. until reaction completion, generally 15-18 hr. The reaction mixture was quenched with water. Ethanol was removed by distillation to about 5 volumes. The product was isolated by filtration, washed with water and dried in a vacuum oven. The yield was 88-95%.

Workup

  1. customThe resulting solution was held at 60° C. until reaction completion, generally 15-18 hr
  2. customThe reaction mixture was quenched with water
  3. customEthanol was removed by distillation to about 5 volumes
  4. customThe product was isolated by filtration
  5. washwashed with water
  6. customdried in a vacuum oven

Sources & evidence

ORD record
ord-b9cb9cc2d0f24b9d84b3837a460eacaf
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Linked notes

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