Methyl iodide → 2-[2(Methylamino)phenyl]-2-oxoethyl benzoate

HRID 358654Notes

Reaction equation

HRID 358654 reaction equation
IC.[C:3]([O:11][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21])=[O:14])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:22](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:3]([O:11][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21][CH3:22])=[O:14])(=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 271530922-(2-Aminophenyl)-2-oxoethyl benzoate

Product 1

HCID 679300742-[2(Methylamino)phenyl]-2-oxoethyl benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodomethane (55.8 ml) was added to a stirred suspension of 2-(2-aminophenyl)-2-oxoethyl benzoate (109 g) and potassium carbonate (1 )8 g) in dry dimethylformamide (400 ml) at ambient temperature. The mixture was stirred at this temperature for 21hours and then at 40° for 5 hours. The solvent was removed under reduced pressure at 60°, water (100 ml) was added and the mixture extracted with dichloromethane (3×200 ml). The combined extracts were dried over sodium sulphate and the solvent was removed by evaporation to leave a dark oil. The oil was purified by flash chromatography on a silica gel column eluted with dichloromethane to give the novel compound 2-[2(methylamino)phenyl]-2-oxoethyl benzoate, m.p. 85°-87°.

Workup

  1. waitat 40° for 5 hours
  2. customThe solvent was removed under reduced pressure at 60°
  3. additionwater (100 ml) was added
  4. extractionthe mixture extracted with dichloromethane (3×200 ml)
  5. dry with materialThe combined extracts were dried over sodium sulphate
  6. customthe solvent was removed by evaporation
  7. customto leave a dark oil
  8. customThe oil was purified by flash chromatography on a silica gel column
  9. washeluted with dichloromethane

Sources & evidence

ORD record
ord-b30bc81014514b848dcf8c36ca1eb807
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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