Ethanol → Ethyl 3-(4-fluorophenyl)-1h-pyrazole-5-carboxylate

HRID 2110875Notes

Reaction equation

HRID 2110875 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([CH2:8][C:9](=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=O)=[CH:4][CH:3]=1.O.[NH2:19][NH2:20].C(O)C>O>[F:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]2[CH:8]=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[NH:20][N:19]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 596593Ethyl 4-(4-fluorophenyl)-2,4-dioxobutanoate

Product 1

HCID 583549Ethyl 3-(4-fluorophenyl)-1h-pyrazole-5-carboxylateYield 99.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 3-(4-fluorobenzoyl)pyruvate (11.3 g, 47.4 mmol), hydrazine monohydrate (2.50 g, 50.0 mmol) and ethanol (50 mL) was heated under reflux for 1 hr. The reaction mixture was cooled and poured into water. The precipitated solid was collected by filtration, washed with water, and dried to give the title compound (11.0 g, quantitative) as colorless crystals. 1H NMR (CDCl3) δ: 1.41 (3H, t, J=7.2 Hz), 4.41 (2H, q, J=7.2 Hz), 7.05-7.18 (3H, m), 7.76 (2H, dd, J=8.2, 5.4 Hz), 11.21 (1H, s).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hr
  3. temperatureThe reaction mixture was cooled
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-10b9ba4e2b034199865af00934991af1
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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