Ethyl [(5-methoxy-2-nitrobenzyl)-(4-chlorobenzoyl)amino]acetate → Ethyl [(2-amino-5-methoxybenzyl)-(4-chlorobenzoyl)amino]acetate

HRID 2417523Notes

Reaction equation

HRID 2417523 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:26]([O-])=O)=[C:7]([CH:25]=1)[CH2:8][N:9]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1.[H][H]>C(OCC)(=O)C.C(O)C.[Pd]>[NH2:26][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:25][C:7]=1[CH2:8][N:9]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1

Participants

6

Reactant 2

HCID 86589884Ethyl [(5-methoxy-2-nitrobenzyl)-(4-chlorobenzoyl)amino]acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 86589885Ethyl [(2-amino-5-methoxybenzyl)-(4-chlorobenzoyl)amino]acetate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.0 g (2.5 mmol) of ethyl [(5-methoxy-2-nitrobenzyl)-(4-chlorobenzoyl)amino]acetate was dissolved in a mixture of 10 ml of ethyl acetate and 10 ml of ethanol. 360 mg of 10% palladium/carbon was added to the obtained solution, and they were stirred in the presence of hydrogen at room temperature for 4 hours. The reaction mixture was filtered through Celite and the solvent was evaporated. The obtained crude product was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent was evaporated
  3. customThe obtained crude product
  4. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-d6ddc8b75888403cadf7e265cf68bd1e
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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