Hydrazine hydrate (1:1) → 5-Methyl-5-trifluoromethyl-pyrazolidin-3-one

HRID 240488Notes

Reaction equation

C([O:3][C:4](=O)[CH:5]=[C:6]([CH3:11])[C:7]([F:10])([F:9])[F:8])C.O.[NH2:14][NH2:15]>C(O)C>[CH3:11][C:6]1([C:7]([F:10])([F:9])[F:8])[NH:15][NH:14][C:4](=[O:3])[CH2:5]1

Participants

Conditions

Temperature: 80 °C

Procedure

(300 mg, 1.65 mmol) 4,4,4-Trifluoro-3-methyl-but-2-enoic acid ethyl ester (CAS 24490-03-7) was dissolved in ethanol (3 ml) and hydrazine monohydrate 64% in ethanol (0.13 ml, 1.73 mmol, 1.05 equiv.) was added at room temperature and stirred in a sealed tube for 16 hours at 80° C. The reaction mixture was evaporated to dryness. The desired (RS)-5-methyl-5-trifluoromethyl-pyrazolidin-3-one (280 mg, quant.) was obtained as a white solid, MS: m/e=169.2 (M+H+).

Workup

customThe reaction mixture was evaporated to dryness

Sources & evidence

ORD record: ord-63b613c9e5434d1e91a16e0665d8827c
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648088B2

Reaction notes

Loading…