Ethyl N-(2,3-dichloro-6-nitrobenzyl)glycine → ethyl-N-(6-amino-2,3-dichlorobenzyl)glycine

HRID 1935670Notes

Reaction equation

HRID 1935670 reaction equation
[CH2:1]([N:3]([CH2:8][C:9]1[C:14]([N+:15]([O-])=O)=[CH:13][CH:12]=[C:11]([Cl:18])[C:10]=1[Cl:19])[CH2:4][C:5]([OH:7])=[O:6])[CH3:2]>[Pt]>[CH2:1]([N:3]([CH2:8][C:9]1[C:14]([NH2:15])=[CH:13][CH:12]=[C:11]([Cl:18])[C:10]=1[Cl:19])[CH2:4][C:5]([OH:7])=[O:6])[CH3:2]

Participants

3

Reactant 1

HCID 22439334Ethyl N-(2,3-dichloro-6-nitrobenzyl)glycine2×

Product 1

HCID 67080112ethyl-N-(6-amino-2,3-dichlorobenzyl)glycine

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Procedure

Ethyl N-(2,3-dichloro-6-nitrobenzyl)glycine (compound VI) may also be catalytically hydrogenated using a sulfided platinum on carbon catalyst under hydrogen pressure. The catalyst is then removed by filtration and the filtrate concentrated, diluted with water and an organic solvent and basified using an alkali to a pH of about 9-10. The organic phase is separated and concentrated and the crude material purified by low temperature recrystallization to give ethyl-(6-amino-2,3-dichlorobenzyl)glycine (compound I).

Workup

  1. customThe catalyst is then removed by filtration
  2. concentrationthe filtrate concentrated
  3. additiondiluted with water
  4. customThe organic phase is separated
  5. concentrationconcentrated
  6. customthe crude material purified by low temperature recrystallization

Sources & evidence

ORD record
ord-cd52059c5e3a4b1e876432fbeb5435d3
Source dataset
uspto-grants-2002_05
Patent number
US06388073B1

Reaction notes

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