Ethyl bromoacetate → {[2-(2-Chloro-6-nitro-phenyl)-ethyl]-methyl-amino}-acetic Acid Ethyl Ester

HRID 1743839Notes

Reaction equation

HRID 1743839 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH2:11][CH2:12][NH:13][CH3:14].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][N:13]([CH2:12][CH2:11][C:3]1[C:4]([N+:8]([O-:10])=[O:9])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[CH3:14])[CH3:21]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 22236581[2-(2-Chloro-6-nitrophenyl)ethyl](methyl)amine

Product 1

HCID 69549902{[2-(2-Chloro-6-nitro-phenyl)-ethyl]-methyl-amino}-acetic Acid Ethyl EsterYield 58.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of [2-(2-chloro-6-nitro-phenyl)-ethyl]-methylamine (11.0 g, 0.051 mole) and ethyl bromoacetate (8.56 g, 0.051 mole) in acetonitrile (200 mL) containing potassium carbonate (3.54 g, 0.026 mole) was stirred at room temperature overnight. The mixture was evaporated in vacuo, water was added to the residue, this mixture was made basic with sodium carbonate and then extracted with dichloromethane (2×300 mL), the combined organic layers were washed with saturated sodium chloride (300 mL), dried and concentrated. Purification by flash column chromatography (silica gel, methylene chloride:hexanes 1:1) provided 9.0 g of the title compound as a light brown oil. 1H NMR (CDCl3): 7.70 δ (d, 1H); 7.60 δ (d, 1H); 7.35 δ (t, 1H); 4.20 δ (m, 2H); 3.35 δ (s, 2H); 3.15 δ (t, 2H); 2.90 δ (t, 2H); 2.50 δ (s, 3H); 1.30 δ (t, 3H).

Workup

  1. customThe mixture was evaporated in vacuo, water
  2. additionwas added to the residue
  3. extractionextracted with dichloromethane (2×300 mL)
  4. washthe combined organic layers were washed with saturated sodium chloride (300 mL)
  5. customdried
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (silica gel, methylene chloride:hexanes 1:1)

Sources & evidence

ORD record
ord-d16e032a50584ca3bb7d8d3f1c595be2
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

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