2-Chloroethyl methyl ether → 6-(4-chlorobenzoyl)-4-(3-chlorophenyl)-1-(2-methoxyethyl)-2(1H)-quinolinone

HRID 1739832Notes

Reaction equation

HRID 1739832 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:29]=[CH:28][C:7]([C:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[NH:16][C:15](=[O:20])[CH:14]=[C:13]3[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)=[O:9])=[CH:6][CH:5]=1.[CH3:30][O:31][CH2:32][CH2:33]Cl>CS(C)=O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH2:33][CH2:32][O:31][CH3:30])[C:15](=[O:20])[CH:14]=[C:13]3[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)=[O:9])=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 123162-Chloroethyl methyl etherHCID 24758Sodium hydrideHCID 155243306-(4-chlorobenzoyl)-4-(3-chlorophenyl)-2(1H)-quinolinone

Product 1

HCID 218374826-(4-chlorobenzoyl)-4-(3-chlorophenyl)-1-(2-methoxyethyl)-2(1H)-quinolinoneYield 36%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium hydride (601 g) was added portionwise under N2 flow to a solution of interm. (9-d) (15 g) in dimethyl sulfoxide (200 ml). The mixture was stirred at room temperature for 30 minutes. 2-Chloroethyl methyl ether (25.2 ml) was added. The mixture was stirred at 50° C. for 72 hours, poured out on ice and extracted with ethyl acetate. The organic layer was separated, washed with water, dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: cyclohexane/ethyl acetate 70/30). The pure fractions were collected and the solvent was evaporated, yielding 6.2 g (36%) of 6-(4-chlorobenzoyl)-4-(3-chlorophenyl)-1-(2-methoxyethyl)-2(1H)-quinolinone (interm. 9-e).

Workup

  1. stirringThe mixture was stirred at 50° C. for 72 hours
  2. additionpoured out on ice
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by column chromatography over silica gel (eluent: cyclohexane/ethyl acetate 70/30)
  10. customThe pure fractions were collected
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a68cd66e68bb448b8df98e3623628a01
Source dataset
uspto-grants-1999_10
Patent number
US05968952

Reaction notes

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