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

HRID 2102304Notes

Reaction equation

HRID 2102304 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-carboxylateYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(3-chloro-phenyl)-2,4-dioxo-butyric acid ethyl ester (3.0 g, 11.8 mmol) and hydroxylamine hydrochloride (2.46 g, 35.4 mmol) in methanol (60 ml) was heated at 80° C. for 4 h. After cooling, the mixture was filtered and washed with cold methanol to afford 5-(3-chloro-phenyl)-isoxazole-3-carboxylic acid ethyl ester (2.0 g, 71%, white solid). 1H NMR (CDCl3) d (ppm): 7.82 (s, 1H), 7.72 (m, 1H), 7.47 (m, 2H), 4.03 (s, 3H). Mixture of both methyl and ethyl ester (mostly methyl).

Workup

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

Sources & evidence

ORD record
ord-21fb34453f1c4e8696306292cd9573e3
Source dataset
uspto-grants-2009_08
Patent number
US07576077B2

Reaction notes

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