Ammonium Chloride → Tert-butyl 4-aminophenethylcarbamate

HRID 557348Notes

Reaction equation

HRID 557348 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-]>CCO.O.[Fe]>[NH2:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:16][CH:15]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 10264884Tert-butyl N-[2-(4-nitrophenyl)ethyl]carbamate

Product 1

HCID 382207Tert-butyl 4-aminophenethylcarbamate

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (tert-butoxy)-N-[2-(4-nitrophenyl)ethyl]-carboxamide (570 mg, 2.15 mmol, Step A), iron powder (602 mg, 10.75 mmol) and NH4Cl (82 mg, 1.5 mmol) in EtOH (6 mL) and H2O (6 ml) was stirred for 4 h at 80° C. Filtration and concentration gave the crude compound, which was used in next step without further purification.

Workup

  1. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-882581988480452a9e786ff4ef262e6d
Source dataset
uspto-grants-2011_11
Patent number
US08058445B2

Reaction notes

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