Diphenyl Ether → 3-butyryl-8-phthalimido-4(1H)quinolone

HRID 1090669Notes

Reaction equation

HRID 1090669 reaction equation
[C:1]([C:6](=[CH:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30])[C:7]([O:9]CC)=O)(=[O:5])[CH2:2][CH2:3][CH3:4].C1(OC2C=CC=CC=2)C=CC=CC=1>CCCCCC>[C:1]([C:6]1[C:7](=[O:9])[C:19]2[C:14](=[C:15]([N:20]3[C:24](=[O:25])[C:23]4=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]4[C:21]3=[O:30])[CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 178450491HCID 178450491, compound

Product 1

HCID 103385613-butyryl-8-phthalimido-4(1H)quinolone

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Ethyl 2-butyryl-3-(2-phthalimidophenylamino)acrylate (83 g, 0.2 mol) was added portionwise to boiling diphenyl ether and heated under reflux for 45 mins. The mixture was cooled, diluted with hexane and the 3-butyryl-8-phthalimido-4(1H)quinolone (50 g, 67.5%) filtered off, washed with hexane and dried, m.p. 318°-20° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 45 mins
  3. temperatureThe mixture was cooled
  4. filtrationthe 3-butyryl-8-phthalimido-4(1H)quinolone (50 g, 67.5%) filtered off
  5. washwashed with hexane
  6. customdried

Sources & evidence

ORD record
ord-4efe4ade941d48beb5e6e8dc60e473da
Source dataset
uspto-grants-1992_01
Patent number
US05082841

Reaction notes

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