Ethyl bromoacetate → {[2-(4-Chloro-2-nitro-phenyl)-ethyl]-methyl-amino}-acetic Acid Ethyl Ester

HRID 1743871Notes

Reaction equation

HRID 1743871 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][CH3:11])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.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:10]([CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[N+:12]([O-:14])=[O:13])[CH3:11])[CH3:21]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 22236591[2-(4-Chloro-2-nitrophenyl)ethyl](methyl)amine

Product 1

HCID 69550684{[2-(4-Chloro-2-nitro-phenyl)-ethyl]-methyl-amino}-acetic Acid Ethyl EsterYield 53.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of [2-(4-chloro-2-nitro-phenyl)-ethyl]-methyl-amine (29.8 g, 0.14 mole) and ethyl bromoacetate (23.2 g, 0.14 mole) in acetonitrile (500 mL) containing potassium carbonate (9.6 g, 0.07 mole) was stirred at room temperature overnight. The mixture was evaporated in vacuo, water was added to the residue and then extracted with dichloromethane (2×200 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) provided 22.5 g of the title compound as a brown oil. 1H NMR (DMSO): 7.98 δ (d, 1H); 7.68 δ (dd, 1H); 7.52 δ (d, 1H); 4.00 δ (m, 2H); 3.20 δ (s, 2H); 2.88 δ (t, 2H); 2.68 δ (t, 2H); 2.25 δ (s, 3H); 1.10 δ (t, 3H).

Workup

  1. customThe mixture was evaporated in vacuo, water
  2. additionwas added to the residue
  3. extractionextracted with dichloromethane (2×200 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)

Sources & evidence

ORD record
ord-b490eceb751f406ca5846828f1de7407
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

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