n-[2-(3-Methoxybenzoyl)-4-[2-(4-chlorophenyl)-1,3-dioxolan-2-yl]phenyl]acetamide → 6-[2-(4-Chlorophenyl)-1,3-dioxolan-2-yl]-4-(3-methoxyphenyl)-2(1h)-quinolinone

HRID 840156Notes

Reaction equation

HRID 840156 reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:36]=[CH:37][CH:38]=1)[C:12]([C:14]1[CH:19]=[C:18]([C:20]2([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[O:24][CH2:23][CH2:22][O:21]2)[CH:17]=[CH:16][C:15]=1[NH:32][C:33](=[O:35])[CH3:34])=O>COCCOC>[Cl:31][C:28]1[CH:27]=[CH:26][C:25]([C:20]2([C:18]3[CH:19]=[C:14]4[C:15](=[CH:16][CH:17]=3)[NH:32][C:33](=[O:35])[CH:34]=[C:12]4[C:11]3[CH:36]=[CH:37][CH:38]=[C:9]([O:8][CH3:7])[CH:10]=3)[O:21][CH2:22][CH2:23][O:24]2)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 22714356n-[2-(3-Methoxybenzoyl)-4-[2-(4-chlorophenyl)-1,3-dioxolan-2-yl]phenyl]acetamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 227143486-[2-(4-Chlorophenyl)-1,3-dioxolan-2-yl]-4-(3-methoxyphenyl)-2(1h)-quinolinoneYield 123%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Potassium tert-butoxide (33 g) was added portionwise at room temperature to a solution of interm. (5-d) (36.4 g) in 1.2-dimethoxyethane (350 ml) and the mixture was stirred at room temperature overnight. The mixture was hydrolized and extracted with DCM. The organic layer was dried, filtered off and evaporated till dryness. The product was used without further purification, yielding 43 g of 6-[2-(4-chloro-phenyl)-1,3-dioxolan-2-yl]-4-(3-methoxyphenyl)-2(1H)-quinolinone (interm. 5-e).

Workup

  1. extractionextracted with DCM
  2. customThe organic layer was dried
  3. filtrationfiltered off
  4. customevaporated till dryness
  5. customThe product was used without further purification

Sources & evidence

ORD record
ord-ba894179d6dc47d5b3d9a0037e43a51f
Source dataset
uspto-grants-2002_04
Patent number
US06365600B1

Reaction notes

Loading…