Methyl Acrylate → HCID 13180328, compound

HRID 1075188Notes

Reaction equation

HRID 1075188 reaction equation
[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[Cl:13][C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[C:19]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:20](=[O:24])[NH:21]2)=[CH:16][CH:15]=1.[C:31]([O:35][CH3:36])(=[O:34])[CH:32]=[CH2:33]>>[CH3:36][O:35][C:31](=[O:34])[CH2:32][CH2:33][N:21]1[C:22]2[C:17](=[CH:16][CH:15]=[C:14]([Cl:13])[CH:23]=2)[CH:18]=[C:19]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:20]1=[O:24]

Participants

4

Reactant 3

HCID 7294Methyl AcrylateHCID 66854Benzyltrimethylammonium hydroxideHCID 122780387-chloro-3-phenyl-1H-quinolin-2-one

Product 1

HCID 13180328HCID 13180328, compound

Procedure

1 ml of benzyltrimethylammonium hydroxide is added to a suspension of 8 g of 7-chloro-1,2-dihydro-2-oxo-3-phenylquinoline in 21.3 ml of methyl acrylate at 40° to 50° C., under nitrogen, the mixture is stirred at this temperature for 31/2 hours and the excess methyl acrylate is then distilled off in vacuo. The solid residue is dissolved in 100 ml of methylene chloride and the solution is washed with 2 N acetic acid, sodium bicarbonate solution and water. After drying the organic phase over sodium sulphate and distilling off the solvent, the residue is recrystallised from cyclohexane. 8.0 g of the title compound of m. 122°-124° C. are obtained.

Workup

  1. distillationthe excess methyl acrylate is then distilled off in vacuo
  2. dissolutionThe solid residue is dissolved in 100 ml of methylene chloride
  3. washthe solution is washed with 2 N acetic acid, sodium bicarbonate solution and water
  4. dry with materialAfter drying the organic phase over sodium sulphate
  5. distillationdistilling off the solvent
  6. customthe residue is recrystallised from cyclohexane
  7. custom122°-124° C. are obtained

Sources & evidence

ORD record
ord-62551d41c6fd4476a41dd69db2bdac0c
Source dataset
uspto-grants-1983_07
Patent number
US04395414

Reaction notes

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