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 1636910Notes

Reaction equation

HRID 1636910 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-0bee72eaf1464f3ba41390d4e1b07a55
Source dataset
uspto-grants-2000_03
Patent number
US06037350

Reaction notes

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