Hydroxyamine hydrochloride → Ethyl 5-(4-chlorophenyl)-4-methylisoxazole-3-carboxylate

HRID 1510430Notes

Reaction equation

HRID 1510430 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])[CH:9]([CH3:17])[C:10](=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1.Cl.[NH2:20]O>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:18][N:20]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:9]=2[CH3:17])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 5051380Ethyl 4-(4-chlorophenyl)-3-methyl-2,4-dioxobutanoate

Product 1

HCID 67121076Ethyl 5-(4-chlorophenyl)-4-methylisoxazole-3-carboxylateYield 3.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The lithium enolate of ethyl 4-(4-chlorophenyl)-3-methyl-2,4-dioxobutanoate (1.5 g, 5.5 mmol) and hydroxylamine hydrochloride (0.46 g, 6.6 mmol) in absolute ethanol (30 mL) were heated to reflux for 17 hours, cooled to room temperature, then cooled to 0° C. for 3 hours. The resulting white crystals were collected and dried under vacuum to obtain ethyl 5-(4-chlorophenyl)-4-methylisoxazole-3-carboxylate (0.55 g, 0.20 mmol).

Workup

  1. temperatureto reflux for 17 hours
  2. temperaturecooled to 0° C. for 3 hours
  3. customThe resulting white crystals were collected
  4. customdried under vacuum

Sources & evidence

ORD record
ord-d664394c9fa947bf90b467bb07255144
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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