Hydroxyamine hydrochloride → HCID 22831984, compound

HRID 340888Notes

Reaction equation

HRID 340888 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8](=[O:17])[CH2:9][C:10](=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:6][CH:7]=1.Cl.[NH2:19]O>CCO>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[O:17][N:19]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 596592HCID 596592, compound

Product 1

HCID 22831984HCID 22831984, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 4-(3-fluorophenyl)-2,4-dioxobutanoate (30.0 g, 126 mmol) in EtOH (300 mL) was added hydroxylamine hydrogen chloride (17 g, 252 mmol). The mixture was stirred at 80° C. for 1 h. The mixture was concentrated to 80 mL and diluted with H2O (100 mL). The precipitate was filtered and washed with H2O to give ethyl 5-(3-fluorophenyl)isoxazole-3-carboxylate (25.8 g, 87%). LRMS (M+H+) m/z 236.0.

Workup

  1. concentrationThe mixture was concentrated to 80 mL
  2. additiondiluted with H2O (100 mL)
  3. filtrationThe precipitate was filtered
  4. washwashed with H2O

Sources & evidence

ORD record
ord-09817c008cb1447b90866de14fb0f00f
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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