HCID 178471919, compound → HCID 10262793, compound

HRID 1382306Notes

Reaction equation

HRID 1382306 reaction equation
[C:1]([C:4](=[CH:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])[C:5]([O:7]CC)=O)(=[O:3])[CH3:2]>C1(OC2C=CC=CC=2)C=CC=CC=1>[C:1]([C:4]1[C:5](=[O:7])[C:17]2[C:12](=[C:13]([O:18][CH3:19])[CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 178471919HCID 178471919, compound

Product 1

HCID 10262793HCID 10262793, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

Ethyl 2-acetyl-3-(2-methoxyphenylamino)acrylate (48 g) was added in portions to boiling diphenyl ether (250 ml) and the mixture heated under reflux for 1 hour. The mixture was cooled and crystallised from a 1:1 mixture of ether and petroleum ether. The solid was filtered off and triturated with boiling ethanol to give 3-acetyl-8-methoxy-4(1H)-quinolone as a brown solid (12.1 g, 31%), m.p. 287°-289°.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 1 hour
  3. temperatureThe mixture was cooled
  4. customcrystallised from a 1:1 mixture of ether and petroleum ether
  5. filtrationThe solid was filtered off
  6. customtriturated with boiling ethanol

Sources & evidence

ORD record
ord-c6dd60f3a7cf43abb92d5662460e7bda
Source dataset
uspto-grants-1989_02
Patent number
US04806550

Reaction notes

Loading…