N,N-Diethylaniline → Methyl 3-(3-hexenyl)-4-acetylamino-5-chlorosalicylate

HRID 1606905Notes

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.CCN([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)CC>C(OC(=O)C)C.CCCCCC>[CH2:30]([C:17]1[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]=1[OH:7])[CH2:29][CH:28]=[CH:33][CH2:32][CH3:31]

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 diethylaniline is placed under house vaccum and heated to 220° C. for 2 hours. This reaction mixture is then diluted with 40% ethylacetate/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-hexenyl)-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-15e96e9fb3f347428c9c78b1d332432b
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04863921

Reaction notes

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