Ammonium Chloride → HCID 53724611, compound

HRID 963510Notes

Reaction equation

HRID 963510 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[CH2:10][NH:11][C:12](=[O:22])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+]>C(O)C.[Fe]>[CH2:1]([O:8][C:9](=[O:23])[CH2:10][NH:11][C:12](=[O:22])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 7843604HCID 7843604, compound

Product 1

HCID 53724611HCID 53724611, compoundYield 74.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-(3-nitrobenzoyl)glycine benzyl ester (5.98 g) in 90% aqueous ethanol (150 ml) was added ammonium chloride (3.56 g). To the mixture was added portionwise iron powder (5.31 g) under stirring and refluxing. After the addition was completed, the mixture was refluxed for 2 hours under stirring. The reaction mixture was hot-filtered. The filtrate and the washings were combined and evaporated in vacuo. To the aqueous residue were added water and ethyl acetate under stirring. The separated organic layer was washed with water twice and dried over magnesium sulfate. Removal of the solvent gave N-(3-aminobenzoyl)glycine benzyl ester (4.03 g) as a viscous oil, which was used in a following reaction without further purification.

Workup

  1. temperaturerefluxing
  2. additionAfter the addition
  3. temperaturethe mixture was refluxed for 2 hours
  4. stirringunder stirring
  5. filtrationThe reaction mixture was hot-filtered
  6. customevaporated in vacuo
  7. additionTo the aqueous residue were added water and ethyl acetate
  8. stirringunder stirring
  9. washThe separated organic layer was washed with water twice
  10. dry with materialdried over magnesium sulfate
  11. customRemoval of the solvent

Sources & evidence

ORD record
ord-8debeea6957548bd950a08a5442aa6c4
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

Loading…