Hydroxyamine hydrochloride → Ethyl 5-(3-chlorophenyl)isoxazole-3-carboxylate

HRID 1453797Notes

Reaction equation

HRID 1453797 reaction equation
[Cl: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>C(O)C>[Cl: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 11054223Ethyl 4-(3-chlorophenyl)-2,4-dioxobutanoate

Product 1

HCID 46929188Ethyl 5-(3-chlorophenyl)isoxazole-3-carboxylateYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of crude ethyl 4-(3-chlorophenyl)-2,4-dioxobutanoate (max 294 g, 1.16 mol) and hydroxylamine hydrochloride (120.4 g, 1.73 mol) in ethanol (4 L) was heated at 80° C. for 4 h. After cooling (over night) to ca 5-10° C., the mixture was filtered, washed with cold ethanol and dried in vacuo to afford the title compound (214.5 g, 74%). 1H NMR: 7.82 (s, 1H), 7.72 (m, 1H), 7.47 (m, 2H), 4.03 (s, 3H). MS (M++1)=252.

Workup

  1. temperatureAfter cooling (over night) to ca 5-10° C.
  2. filtrationthe mixture was filtered
  3. washwashed with cold ethanol
  4. customdried in vacuo

Sources & evidence

ORD record
ord-51209518347b42aaafd0b24bd6c3d75d
Source dataset
uspto-grants-2009_01
Patent number
US07476684B2

Reaction notes

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