Ammonium Chloride → HCID 54284378, compound

HRID 963512Notes

Reaction equation

HRID 963512 reaction equation
[CH2:1]([O:8][C:9](=[O:24])[C@H:10]([CH3:23])[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:24])[C@H:10]([CH3:23])[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 8883831HCID 8883831, compound

Product 1

HCID 54284378HCID 54284378, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-(3-nitrobenzoyl)-L-alanine benzyl ester (5.0 g, 15.2 mmol) and ammonium chloride (8.2 g, 0.152 mol) in 90% aqueous ethanol (150 ml) was added portionwise iron powder (4.25 g, 76.1 mmol) under refluxing and stirring, which were continued for an additional 1 hour. The mixture was hot-filtered through Celite® (Johns Manville) and washed with hot aqueous ethanol. The filtrate was evaporated in vacuo to give a residue, which was extracted with ethyl acetate and the organic extract was washed with brine twice. After drying over MgSO4, the solvent was removed in vacuo to afford a viscous oil, which was crystallized soon on standing to give N-(3-aminobenzoyl)-L-alanine benzyl ester (4.5 g, 99.2% yield).

Workup

  1. temperatureunder refluxing
  2. filtrationThe mixture was hot-filtered through Celite® (Johns Manville)
  3. washwashed with hot aqueous ethanol
  4. customThe filtrate was evaporated in vacuo
  5. customto give a residue, which
  6. extractionwas extracted with ethyl acetate
  7. extractionthe organic extract
  8. washwas washed with brine twice
  9. dry with materialAfter drying over MgSO4
  10. customthe solvent was removed in vacuo
  11. customto afford a viscous oil, which
  12. customwas crystallized soon

Sources & evidence

ORD record
ord-1235170a72554fadaaa93c5c6b6b8b51
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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