HCID 178471921, compound → 3-cyclohexylcarbonyl-8-methoxy-4(1H)-quinolone

HRID 1382267Notes

Reaction equation

HRID 1382267 reaction equation
[CH:1]1([C:7]([C:9](=[CH:15][NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[C:10]([O:12]CC)=O)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH:1]1([C:7]([C:9]2[C:10](=[O:12])[C:22]3[C:17](=[C:18]([O:23][CH3:24])[CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 1

HCID 178471921HCID 178471921, compound

Product 1

HCID 100167833-cyclohexylcarbonyl-8-methoxy-4(1H)-quinoloneYield 35.2%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

Ethyl 2-cyclohexylcarbonyl-3-(2-methoxyphenylamino)acrylate (20 g, 0.06 mol) was added in portions to boiling diphenyl ether (200 ml) and the mixture was heated under reflux for 1.5 hours. When cool, the mixture was diluted with petroleum ether and allowed to crystallise overnight to give 3-cyclohexylcarbonyl-8-methoxy-4(1H)-quinolone (6.0 g, 35.2%), m.p. 168°-70° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureWhen cool
  4. customto crystallise overnight

Sources & evidence

ORD record
ord-21a8ca2d744a4e3a93dc2a7fa5099ca2
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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