Hydrazine → HCID 57947719, compound

HRID 409753Notes

Reaction equation

HRID 409753 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:12]=[C:11]([C:13]([O:15]C)=O)[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.FC1C=C(C2C=C(C(O)=O)ON=2)C=CC=1.S(Cl)(Cl)=O.[NH2:36][NH2:37]>CO>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:12]=[C:11]([C:13]([NH:36][NH2:37])=[O:15])[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 9321HydrazineHCID 24386Thionyl ChlorideHCID 65042203-(3-Fluorophenyl)-5-isoxazolecarboxylic acidHCID 57947829HCID 57947829, compound

Product 1

HCID 57947719HCID 57947719, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of methyl 3-(3-fluorophenyl)isoxazole-5-carboxylate (prepared according to the literature method: T. T. Dang, U. Albrecht and P. Langer, Preparation 2006, No. 15, 2515-252; or treatment of 3-(3-fluorophenyl)isoxazole-5-carboxylic acid with thionyl chloride and methanol) (5.55 g, 25 mmol, 1.0 equiv.), hydrazine (960 mg, 30 mmol) and MeOH (100 mL) was refluxed for 1 h and concentrated. The residue was washed with dichloromethane and dried in vacuum to give 3-(3-fluorophenyl)isoxazole-5-carbohydrazide (5.6 g, quant.). LRMS (M+H+) m/z 222.0

Workup

  1. customprepared
  2. customLanger, Preparation 2006
  3. concentrationconcentrated
  4. washThe residue was washed with dichloromethane
  5. customdried in vacuum

Sources & evidence

ORD record
ord-3b6d6f415f7645968945047adae55740
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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