Potassium Carbonate → 6-(4-Chlorobenzoyl)-4-(3-hydroxyphenyl)-1-methyl-2(1h)-quinolinone

HRID 1739827Notes

Reaction equation

HRID 1739827 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][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]C)[CH:21]=2)=[O:7])=[CH:4][CH:3]=1.BrB(Br)Br.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[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]([OH:26])[CH:21]=2)=[O:7])=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 25134Boron tribromideHCID 227143576-(4-Chlorobenzoyl)-4-(3-methoxyphenyl)-1-methyl-2(1h)-quinolinone

Product 1

HCID 218374946-(4-Chlorobenzoyl)-4-(3-hydroxyphenyl)-1-methyl-2(1h)-quinolinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Interm. (b 7-g) (6.8 g) was added to DCM (210 ml), stirred at 0° C. Tribromoborane (67.3 ml) was added dropwise and the reaction mixture was stirred at 0° C. for 15 minutes. The mixture was brought to room temperature, stirred at room temperature for 30 minutes and K2CO3 10% was added. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated, yielding 6.6 g of 6-(4-chlorobenzoyl)-4-(3-hydroxyphenyl)-1-methyl-2(1H)-quinolinone (interm. 7-h) (quantitative yield; used in next reaction step, without further purification).

Workup

  1. stirringthe reaction mixture was stirred at 0° C. for 15 minutes
  2. customwas brought to room temperature
  3. stirringstirred at room temperature for 30 minutes
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9ff5f165e57349f69b8cc3dd95260a4a
Source dataset
uspto-grants-1999_10
Patent number
US05968952

Reaction notes

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