Ammonium Chloride → HCID 86729276, compound

HRID 1399873Notes

Reaction equation

HRID 1399873 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:21]([O-])=O)=[C:6]([NH:8][CH:9]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]2)[CH:7]=1.[NH4+].[Cl-]>CCO.[Fe]>[NH2:21][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][C:6]=1[NH:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 71116560HCID 71116560, compound

Product 1

HCID 86729276HCID 86729276, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a solution of tert-butyl 3-((5-bromo-2-nitrophenyl)amino)pyrrolidine-1-carboxylate (crude) (550 mg, 1.5 mmol) in EtOH (10 mL) was added Fe powder (1.27 mg, 22.7 mmol) and NH4Cl (1.20 g, 0.227 mmol, in 10 ml water). After stirring for 4 h at refluxing temperature, the reaction mixture was filtered over a Celite pad and the filtrate concentrated. The residue used for next step without further purification (410 mg, Yield 76%). LCMS (m/z): 356.1 (M+1).

Workup

  1. temperatureat refluxing temperature
  2. filtrationthe reaction mixture was filtered over a Celite pad
  3. concentrationthe filtrate concentrated
  4. customThe residue used for next step without further purification (410 mg, Yield 76%)

Sources & evidence

ORD record
ord-bc254860c61a4349a4fab250d8d894a6
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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