Ethyl benzoylacetate → 3-Phenyl-1H-pyrazol-5-ol

HRID 889903Notes

Reaction equation

HRID 889903 reaction equation
[C:1]([CH2:9][C:10]([O:12]CC)=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].O.[NH2:18][NH2:19]>>[C:2]1([C:1]2[NH:19][NH:18][C:10](=[O:12])[CH:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7170Ethyl benzoylacetateHCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 5947633-Phenyl-1H-pyrazol-5-olYield 81%

Procedure

A vigorously stirred solution of ethyl benzoylacetate (30 g 150 mmol), of 5% aqueous sodium hydroxide (312 mL), and hydrazine hydrate (14.6 mL 468 mmol) was heated to 75° C. for sixteen hours. The resultant precipitate was filtered, washed with water and dried and gave 5-Phenyl-1,2-dihydro-pyrazol-3-one (20.3) in 81% yield as a white solid. C9H8N2O: 1H NMR (d6-DMSO): δ 7.62 (d, 2H, J=7.0 Hz), 7.36 (t, 2H, J=7.0 Hz), 7.26 (t, 1H, J=7.0 Hz), 5.85 (s, 1H) ppm.

Workup

  1. filtrationThe resultant precipitate was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-0ab4e74251f94297b4416e7bf3f5ce9d
Source dataset
uspto-grants-2006_02
Patent number
US06995171B2

Reaction notes

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