Sodium Bicarbonate → Ethyl (5-methyl-2-nitrobenzyl)aminoacetate

HRID 2417501Notes

Reaction equation

HRID 2417501 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH2:7]Cl.Cl.[CH2:14]([O:16][C:17](=[O:20])[CH2:18][NH2:19])[CH3:15].C(=O)([O-])O.[Na+]>C(O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH2:7][NH:19][CH2:18][C:17]([O:16][CH2:14][CH3:15])=[O:20]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 2724031alpha-Chloro-5-methyl-2-nitrotoluene

Product 1

HCID 86217985Ethyl (5-methyl-2-nitrobenzyl)aminoacetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

5.0 g (27 mmol) of 5-methyl-2-nitrobenzyl chloride was dissolved in 100 ml of ethanol. 7.5 g (54 mmol) of glycine ethyl ester hydrochloride and 6.8 g (81 mmol) of sodium hydrogencarbonate were added to the obtained solution, and they were stirred at 70° C. for 6 hours. The solvent was evaporated. After the extraction with ethyl acetate, the extract was washed with 1 N hydrochloric acid. The obtained aqueous layer was made basic with 1 N sodium hydroxide. After the extraction with ethyl acetate, the obtained organic layer was washed with saturated aqueous sodium chloride solution and then dried. The solvent was evaporated to obtain the title compound.

Workup

  1. customThe solvent was evaporated
  2. extractionAfter the extraction with ethyl acetate
  3. washthe extract was washed with 1 N hydrochloric acid
  4. extractionAfter the extraction with ethyl acetate
  5. washthe obtained organic layer was washed with saturated aqueous sodium chloride solution
  6. customdried
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-cca4db19afb44e3eb28baac5f8cab456
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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