Ethyl Acetate → Methyl 2-(methyl(4-nitrobenzyl)amino)acetate

HRID 1776502Notes

Reaction equation

HRID 1776502 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.Cl.[CH3:13][NH:14][CH2:15][C:16]([O:18][CH3:19])=[O:17].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CC#N.O>[CH3:13][N:14]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1)[CH2:15][C:16]([O:18][CH3:19])=[O:17]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromideHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)

Product 1

HCID 18472662Methyl 2-(methyl(4-nitrobenzyl)amino)acetateYield 72.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-(bromomethyl)-4-nitrobenzene (1 g, 4.63 mmol), methyl 2-(methylamino)acetate hydrochloride (0.646 g, 4.63 mmol), and K2CO3 (0.960 g, 6.94 mmol) in CH3CN (20 ml) was heated under MW irradiation at 60° C. for 1.5 hours. The mixture was portioned between EtOAc and water, and the organic layer was washed with brine ad dried over Na2SO4. The solvent was removed and the crude was purified by filtration on SCX cartridge (DCM/MeOH 1/1; MeOH/conc.aq.NH4OH 90/10). The basic fraction was evaporated to dryness to give methyl 2-(methyl(4-nitrobenzyl)amino)acetate (0.800 g, 3.36 mmol, 72.5% yield, MS/ESI+ 239.1 [MH]+).

Workup

  1. washthe organic layer was washed with brine ad
  2. dry with materialdried over Na2SO4
  3. customThe solvent was removed
  4. filtrationthe crude was purified by filtration on SCX cartridge (DCM/MeOH 1/1; MeOH/conc.aq.NH4OH 90/10)
  5. customThe basic fraction was evaporated to dryness

Sources & evidence

ORD record
ord-84c780464016417ca62c8572b597ed56
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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