{[2-(4-Chloro-2-nitro-phenyl)-ethyl]-methyl-amino}-acetic Acid Ethyl Ester → {[2-(4-chloro-2-nitro-phenyl)-ethyl]-methyl-amino}-acetic Acid

HRID 1743872Notes

Reaction equation

HRID 1743872 reaction equation
C([O:3][C:4](=[O:20])[CH2:5][N:6]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[N+:17]([O-:19])=[O:18])[CH3:7])C>Br.C(#N)C>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][CH2:8][N:6]([CH2:5][C:4]([OH:20])=[O:3])[CH3:7])=[C:11]([N+:17]([O-:19])=[O:18])[CH:12]=1

Participants

4

Reactant 1

HCID 69550684{[2-(4-Chloro-2-nitro-phenyl)-ethyl]-methyl-amino}-acetic Acid Ethyl Ester

Product 1

HCID 22236587{[2-(4-chloro-2-nitro-phenyl)-ethyl]-methyl-amino}-acetic Acid

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

{[2-(4-Chloro-2-nitro-phenyl)-ethyl]-methyl-amino}-acetic acid ethyl ester (22.5 g, 0.075 mole) dissolved in concentrated hydrobromic acid (48 wt. % in water, 200 mL) was allowed to stir at 70° C. overnight and then reduced to a small volume in vacuo. The residue oil was taken up in acetonitrile and the solution was evaporated in vacuo. This procedure was repeated until the water was removed and a crystalline residue remained. This material (18.5 g) was used in the next step without further purification.

Workup

  1. customthe solution was evaporated in vacuo
  2. customwas removed
  3. customThis material (18.5 g) was used in the next step without further purification

Sources & evidence

ORD record
ord-5144bf1136cc484e8a01e65a25a3a7c6
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

Loading…