Ethyl-2-(2'-methylbenzoyl)-3-dimethylaminopropenoate → 5-o-Tolylisoxazole-4-carboxylic acid ethyl ester

HRID 1389013Notes

Reaction equation

HRID 1389013 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5]([C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])=[CH:6][N:7](C)C)[CH3:2].C(OC(=O)C(C(=O)C1C=CC=CC=1Cl)=CN(C)C)C>>[CH2:1]([O:3][C:4]([C:5]1[CH:6]=[N:7][O:18][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])=[O:19])[CH3:2]

Participants

3

Reactant 2

HCID 54457205Ethyl-2-(2'-methylbenzoyl)-3-dimethylaminopropenoateHCID 54509863Ethyl 2-(2-chlorobenzoyl)-3-dimethylaminopropenoate

Product 1

HCID 202975005-o-Tolylisoxazole-4-carboxylic acid ethyl esterYield 82.6%

Procedure

The procedure of Example 22 was employed utilizing ethyl-2-(2'-methylbenzoyl)-3-dimethylaminopropenoate in lieu of ethyl-2-(2'-chlorobenzoyl)-3-dimethylaminopropenoate to yield ethyl-5-(2'-methylphenyl)-4-isoxazolecarboxylate (1.9 g.; 82.6% yield) as an oil having the following analysis:

Sources & evidence

ORD record
ord-7d66720156854f54b3d920107ebd130a
Source dataset
uspto-grants-1981_01
Patent number
US04243406

Reaction notes

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