Hydrazine hydrate (1:1) → HCID 68047231, compound

HRID 2283655Notes

Reaction equation

HRID 2283655 reaction equation
O[C:2]1([CH3:20])[O:6][C:5](=O)[CH:4]=[C:3]1[C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]=1[O:18][CH3:19].O.[NH2:22][NH2:23]>C(O)C>[CH3:19][O:18][C:9]1[CH:10]=[CH:11][C:12]([C:14]([F:17])([F:16])[F:15])=[CH:13][C:8]=1[C:3]1[C:2]([CH3:20])=[N:23][NH:22][C:5](=[O:6])[CH:4]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68047230HCID 68047230, compound

Product 1

HCID 68047231HCID 68047231, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

5-Hydroxy-4-[2-methoxy-5-(trifluoromethyl)phenyl]-5-methylfuran-2(5H)-one (Preparation 40, 3 g, 10 mmol) was dissolved in ethanol and cooled to 0° C. Hydrazine monohydrate (1.0 mL, 20 mmol) was added drop-wise to this solution, then the reaction mixture was heated to 90° C. for 16 hours. The reaction mixture was then concentrated in vacuo, azeotoped with toluene and the crude material purified by silica gel column chromatography (ISCO™ Companion, 50% ethyl acetate in heptane elution) to afford the title compound as an off-white solid (1.05 g).

Workup

  1. temperaturethe reaction mixture was heated to 90° C. for 16 hours
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. customthe crude material purified by silica gel column chromatography (ISCO™ Companion, 50% ethyl acetate in heptane elution)

Sources & evidence

ORD record
ord-94f0017f3e1d4c8a8b7c253babdeeaab
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

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