Reaction #302887

ord-a9175d9eed6642e681a9723e72a7b5ad

Reaction equation

CN
methylamine
CCOC(=O)C(=O)c1ccccc1COC
ethyl 2-(2-methoxymethyl-phenyl)-2-oxoacetate
CCOC(=O)C(=O)c1ccccc1COC
( 1 )
CCOC(=O)C(=O)c1ccccc1COC
ethyl 2-(2-methoxymethyl-phenyl)-2-oxoacetate
CO
methanol
CNC(=O)C(=O)c1ccccc1COC
2-(2-methoxymethyl-phenyl)-N-methyl-2-oxo-acetamide

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONwere mixed
  2. 2
    Otherwhile retaining at 25° C.
  3. 3
    Otheran organic layer was recovered
  4. 4
    WashThe organic layer was washed with 178 g of 5% hydrochloric acid, 54.4 g of an aqueous saturated sodium bicarbonate solution, and 54.4 g of water
  5. 5
    Concentrationrespectively, and concentrated with an evaporator

Procedure

28.3 g of the ethyl 2-(2-methoxymethyl-phenyl)-2-oxoacetate obtained in (1), 109 g of toluene, and 54.4 g of methanol were mixed, 28.6 g of a 40% aqueous methylamine solution was added while retaining at 25° C., and the mixture was retained at 25° C. for 2 hours. Thereafter, 54.4 g of water was added, 80 g of toluene were further added, this was allowed to stand still, and an organic layer was recovered. The organic layer was washed with 178 g of 5% hydrochloric acid, 54.4 g of an aqueous saturated sodium bicarbonate solution, and 54.4 g of water, respectively, and concentrated with an evaporator to obtain 12.0 g of 2-(2-methoxymethyl-phenyl)-N-methyl-2-oxo-acetamide.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08192967B2uspto-grants-2012_06