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

HRID 1935675Notes

Reaction equation

HRID 1935675 reaction equation
Cl.[CH2:2]([N:4]([CH2:9][C:10]1[C:15]([N+:16]([O-])=O)=[CH:14][CH:13]=[C:12]([Cl:19])[C:11]=1[Cl:20])[CH2:5][C:6]([OH:8])=[O:7])[CH3:3]>O.C(O)C.[Pt]>[CH2:2]([N:4]([CH2:9][C:10]1[C:15]([NH2:16])=[CH:14][CH:13]=[C:12]([Cl:19])[C:11]=1[Cl:20])[CH2:5][C:6]([OH:8])=[O:7])[CH3:3]

Participants

5

Reactant 1

HCID 66640009ethyl N-(2,3-dichloro-6-nitrobenzyl)glycine hydrochloride2×

Product 1

HCID 67080112ethyl-N-(6-amino-2,3-dichlorobenzyl)glycineYield 72%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 0.344 g of ethyl N-(2,3-dichloro-6-nitrobenzyl)glycine hydrochloride (compound VI) in 1.5 mL of water and 1.5 mL ethanol (with 5% isopropanol) was stirred and 5% sulfided platinum on carbon under hydrogen (50 to 100 psi) for 16 hours. The catalyst was removed by filtration. The filtrate concentrated, diluted with water and toluene, and basified (aqueous sodium hydroxide or potassium carbonate) to pH 9-10. The organic phase was separated, concentrated, and the crude material purified by low-temperature recrystallization from toluene in hexane to give compound I in 72% yield.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationThe filtrate concentrated
  3. additiondiluted with water and toluene, and basified (aqueous sodium hydroxide or potassium carbonate) to pH 9-10
  4. customThe organic phase was separated
  5. concentrationconcentrated
  6. customthe crude material purified by low-temperature recrystallization from toluene in hexane

Sources & evidence

ORD record
ord-9a290401e74b43caa3fd515003f762c7
Source dataset
uspto-grants-2002_05
Patent number
US06388073B1

Reaction notes

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