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

HRID 500524Notes

Reaction equation

HRID 500524 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5](=O)[CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1)=[O:8])[CH3:2].Cl.[NH2:19]O>CO>[CH2:1]([O:3][C:4]([C:5]1[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)[O:8][N:19]=1)=[O:17])[CH3:2]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 11054223Ethyl 4-(3-chlorophenyl)-2,4-dioxobutanoate

Product 1

HCID 46929188Ethyl 5-(3-chlorophenyl)isoxazole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the title compound of Example 3.1 (3.00 g, 11.8 mmol) and hydroxylamine hydrochloride (2.46 g, 35.4 mmol) in methanol (60 mL) was heated at 80° C. for 4 hours. After cooling, the mixture was filtered and washed with cold methanol to afford the title compound in mixture with the methyl ester analog (2.0 g, 71%, white solid).

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. washwashed with cold methanol

Sources & evidence

ORD record
ord-4232581d43ce4bfa8ef3baa0177a8095
Source dataset
uspto-grants-2010_08
Patent number
US07772235B2

Reaction notes

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