4-Fluorophenylhydrazine hydrochloride → HCID 19886173, compound

HRID 654802Notes

Reaction equation

HRID 654802 reaction equation
C([NH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH2:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:6][CH:5]=1)=O.Cl.[F:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][NH2:29])=[CH:24][CH:23]=1>C(O)(=O)C>[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:28]([C:25]3[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=3)[N:29]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 19886129HCID 19886129, compound

Product 1

HCID 19886173HCID 19886173, compoundYield 45.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 4-[4-(formylamino)phenyl]-2,4-dioxobutanoate (6 g) and 4-fluorophenylhydrazine hydrochloride (4.1 g) in acetic acid (30 ml) was stirred at 100° C. for 2 hours. The mixture was concentrated, and the residue was treated with 10% hydrochloric acid (10 ml) and methanol (40 ml) at 60° C. for 2 hours. The solvent was evaporated, and the residue was dissolved in water. The obtained solution was neutralized and extracted with ethyl acetate. The extract was washed with water, dried, and concentrated in vacuo. The residue was washed with ethanol to give crystals of ethyl 5-(4-aminophenyl)-1-(4-fluorophenyl)pyrazole-3-carboxylate (3.4 g).

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was treated with 10% hydrochloric acid (10 ml) and methanol (40 ml) at 60° C. for 2 hours
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in water
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. concentrationconcentrated in vacuo
  9. washThe residue was washed with ethanol

Sources & evidence

ORD record
ord-e184a1af6ed743d0a76ac4b7d804494b
Source dataset
uspto-grants-1992_07
Patent number
US05134142

Reaction notes

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