Methyl 2-(cyclohexen-3-yloxy)-4-acetylamino-5-chlorobenzoate → Methyl 3-(3-Cyclohexenyl)-4-Acetylamino-5-Chlorosalicylate

HRID 5881Notes

Reaction equation

C1CCCC([O:7][C:8]2[CH:17]=[C:16]([NH:18][C:19](=[O:21])[CH3:20])[C:15]([Cl:22])=[CH:14][C:9]=2[C:10]([O:12][CH3:13])=[O:11])C=1>C(OCC)(=O)C.CCCCCC>[CH:16]1([C:17]2[C:16]([NH:18][C:19](=[O:21])[CH3:20])=[C:15]([Cl:22])[CH:14]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[C:8]=2[OH:7])[CH2:15][CH2:14][CH:9]=[CH:8][CH2:17]1

Participants

Conditions

Temperature: 220 °C

Procedure

A mixture of 0.6 g of methyl 2-(cyclohexen-3-yloxy)-4-acetylamino-5-chlorobenzoate and 0.5 ml diethylamiline is placed under house vacuum and heated to 220° C. for 2 hours. This reaction mixture is then diluted with 40% ethyl acetate/hexane and purified by dry column chromatography using the same solvent system as eluent. Three fractions are separated: 1. diethylaniline; 2. starting benzoate compound; and 3. methyl 3-(3-cyclohexenyl)-4-acetylamino-5-chlorosalicylate. The latter is used directly in the next step.

Workup

custompurified
customby dry column chromatography
customThree fractions are separated

Sources & evidence

ORD record: ord-30b84fcc575343ca86cb76a38a32799d
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05246942

Reaction notes

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