Potassium Carbonate → 6-(4-chlorobenzoyl)-1-methyl-4-(3-propoxyphenyl)-2(1H)-quinolinone

HRID 1739828Notes

Reaction equation

HRID 1739828 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13](=[O:19])[CH:12]=[C:11]3[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:29](I)[CH2:30][CH3:31].C([O-])([O-])=O.[K+].[K+]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13](=[O:19])[CH:12]=[C:11]3[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:29][CH2:30][CH3:31])[CH:21]=2)=[O:7])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 218374946-(4-Chlorobenzoyl)-4-(3-hydroxyphenyl)-1-methyl-2(1h)-quinolinone

Product 1

HCID 218374796-(4-chlorobenzoyl)-1-methyl-4-(3-propoxyphenyl)-2(1H)-quinolinoneYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of interm. (7-h) (9.5 g), propyl iodide (5.9 ml) and K2CO3 (10.1 g) was stirred and refluxed for 4 hours. Water was added and the mixture was extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated, yielding 10.4 g (100%) of 6-(4-chlorobenzoyl)-1-methyl-4-(3-propoxyphenyl)-2(1H)-quinolinone (interm. 7-i).

Workup

  1. additionA mixture of interm
  2. temperaturerefluxed for 4 hours
  3. extractionthe mixture was extracted with DCM
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b7b61f2e0b2d4ffbb65ce44b6f7a52a0
Source dataset
uspto-grants-1999_10
Patent number
US05968952

Reaction notes

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