Ammonium Chloride → HCID 86729273, compound

HRID 1051496Notes

Reaction equation

HRID 1051496 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:20]([O-])=O)=[C:6]([NH:8][CH:9]2[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10]2)[CH:7]=1.[NH4+].[Cl-]>CCO.[Fe]>[NH2:20][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][C:6]=1[NH:8][CH:9]1[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 86729272HCID 86729272, compound

Product 1

HCID 86729273HCID 86729273, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a solution of crude tert-butyl 3-((5-bromo-2-nitrophenyl)amino)azetidine-1-carboxylate (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 solution cooled and filtered through a Celite pad and the filtrate concentrated. The residue used directly for next step (400 mg, Yield 78%) without further purification. LCMS (m/z): 342.1 (M+1).

Workup

  1. temperatureat refluxing temperature
  2. temperaturethe solution cooled
  3. filtrationfiltered through a Celite pad
  4. concentrationthe filtrate concentrated
  5. customThe residue used directly for next step (400 mg, Yield 78%) without further purification

Sources & evidence

ORD record
ord-97b3b4e387e74e678714d981e6e0b526
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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