alpha-Bromo-2-nitrotoluene → Ethyl (2-nitrobenzyl)aminoacetate

HRID 2417452Notes

Reaction equation

HRID 2417452 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].[N+:9]([C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14]Br)([O-:11])=[O:10].C(=O)([O-])O.[Na+]>C(O)C>[N+:9]([C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14][NH:7][CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:8])([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 77569alpha-Bromo-2-nitrotolueneHCID 516892Sodium BicarbonateHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 13236074Ethyl (2-nitrobenzyl)aminoacetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

6.35 g (45.4 mmol) of glycine ethyl ester hydrochloride, 2.45 g (11.3 mmol) of 2-nitrobenzyl bromide and 4.75 g (56.5 mmol) of sodium hydrogencarbonate were dissolved in ethanol, and the obtained solution was stirred at 70° C. overnight. The reaction solution was filtered, and the obtained filtrate was treated with ethyl acetate as the extracting solvent by an ordinary method to obtain the crude product. After the purification by the silica gel column chromatography, the title compound was obtained.

Workup

  1. filtrationThe reaction solution was filtered
  2. additionthe obtained filtrate was treated with ethyl acetate as the extracting solvent by an ordinary method
  3. customto obtain the crude product
  4. customAfter the purification by the silica gel column chromatography

Sources & evidence

ORD record
ord-09d7d5fc5903440caa890190c49bcd03
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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