Ammonium Chloride → HCID 86729276, compound

HRID 1051499Notes

Reaction equation

HRID 1051499 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-bc6dd2eb1f51458e8fd2c54c4574a9d8
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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