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 351782Notes

Reaction equation

HRID 351782 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-59f71c67acaf40b4b27bdc3b660c6fcf
Source dataset
uspto-grants-2004_06
Patent number
US06743805B2

Reaction notes

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