Acetic Acid → HCID 178509114, compound

HRID 1708011Notes

Reaction equation

HRID 1708011 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:11](=O)[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[C:9]#[N:10])=[CH:4][CH:3]=1.O.[NH2:20][NH2:21].C(O)(=O)C>C1C=CC=CC=1>[NH2:10][C:9]1[NH:21][N:20]=[C:11]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 141952232-(4-Fluorophenyl)-3-oxo-3-(pyridin-4-yl)propanenitrile

Product 1

HCID 178509114HCID 178509114, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2-(4-fluorophenyl)-3-oxo-3-(pyridin-4-yl)propanenitrile (10 g), hydrazine monohydrate (2.4 ml) and acetic acid (5.2 ml) in dry benzene (100 ml) was refluxed for 4 hours. The reaction mixture was cooled and extracted with 3N-hydrochloric acid (80 ml×3). The extracts were concentrated in vacuo to 100 ml of the volume and the solution was neutralized with aqueous ammonia solution. The separated solid was collected, washed with water and dried to give 5-amino-4-(4-fluorophenyl)-3-(pyridin-4-yl)pyrazole (2.02 g).

Workup

  1. temperaturewas refluxed for 4 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with 3N-hydrochloric acid (80 ml×3)
  4. concentrationThe extracts were concentrated in vacuo to 100 ml of the volume
  5. customThe separated solid was collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-4ef4be1394ea48288fd1467dbf291da1
Source dataset
uspto-grants-1994_10
Patent number
US05356897

Reaction notes

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