Methyl 2-(methyl(4-nitrobenzyl)amino)acetate → HCID 18472314, compound

HRID 1387993Notes

Reaction equation

HRID 1387993 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][N:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1)[CH3:6]>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:17])[CH2:4][N:5]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=1)[CH3:6]

Participants

3

Reactant 1

HCID 18472662Methyl 2-(methyl(4-nitrobenzyl)amino)acetate

Product 1

HCID 18472314HCID 18472314, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In acetic acid (100 ml) was dissolved N-(4-nitro-benzyl)sarcosine methyl ester (5.96 g), and to the mixture was added little by little reduced iron (7 g). The mixture was stirred at room temperature overnight. The solvent was evaporated, and to the residue was added ethyl acetate. The precipitates were filtered off, and the filtrate was washed with sodium hydroxide solution, water and saturated brine, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the resulting residue was purified with silica gel column chromatography (ethyl acetate/hexane) to give N-(4-aminobenzyl)sarcosine methyl ester (3.0 g) as red oil.

Workup

  1. customThe solvent was evaporated
  2. additionto the residue was added ethyl acetate
  3. filtrationThe precipitates were filtered off
  4. washthe filtrate was washed with sodium hydroxide solution, water and saturated brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customUnder reduced pressure, the solvent was evaporated
  7. customthe resulting residue was purified with silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2f81f383a5454736ad11f20bece80c19
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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