6-[2-(4-Chlorophenyl)-1,3-dioxolan-2-yl]-4-(3-methoxyphenyl)-2(1h)-quinolinone → 6-(4-Chlorobenzoyl)-4-(3-methoxyphenyl)-2(1h)-quinolinone

HRID 852273Notes

Reaction equation

HRID 852273 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[NH:19][C:18](=[O:23])[CH:17]=[C:16]4[C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=3)OCC[O:9]2)=[CH:4][CH:3]=1>Cl.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[NH:19][C:18](=[O:23])[CH:17]=[C:16]3[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=2)=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 1

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

Product 1

HCID 227143706-(4-Chlorobenzoyl)-4-(3-methoxyphenyl)-2(1h)-quinolinoneYield 94%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of interm. (5-e) (43 g) in HCl (3N, 400 ml) and methanol (150 ml) was stirred and refluxed overnight. The mixture was cooled and filtered off. The precipitate was washed with water and diethyl ether and dried. The product was used without further purification, yielding 27 g (94%) of 6-(4-chlorobenzoyl)-4-(3-methoxyphenyl)-2(1H)-quinolinone (interm. 5-f).

Workup

  1. additionA mixture of interm
  2. temperaturerefluxed overnight
  3. temperatureThe mixture was cooled
  4. filtrationfiltered off
  5. washThe precipitate was washed with water and diethyl ether
  6. customdried
  7. customThe product was used without further purification

Sources & evidence

ORD record
ord-4d39bd787adb403686aad58177d1c467
Source dataset
uspto-grants-2007_08
Patent number
US07253183B2

Reaction notes

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