Stannous chloride dihydrate → tert-butyl N-((3-aminophenyl)methyl)carbamate

HRID 840589Notes

Reaction equation

HRID 840589 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.O.[Sn](Cl)Cl>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 22620025HCID 22620025, compound

Product 1

HCID 10775412tert-butyl N-((3-aminophenyl)methyl)carbamateYield 100.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(t-butyloxycarbonyl)-3-nitrobenzylamine (13.8 g, 54.7 mmol) in dimethylformamide (200 mL) was added tin(II) chloride dihydrate (74.1 g, 328 mmol) and the reaction was stirred at room temperature for 48 hours. The dimethylformamide was removed under vacuum. The residue was resuspended in dichloromethane (300 ml), washed with brine (200 mL), filtered through a celite pad, and the solvent removed to provide 12.2 g of the title compound. (100%).

Workup

  1. customThe dimethylformamide was removed under vacuum
  2. washwashed with brine (200 mL)
  3. filtrationfiltered through a celite pad
  4. customthe solvent removed

Sources & evidence

ORD record
ord-a48ee9c049854b20952d0b9624409700
Source dataset
uspto-grants-2002_04
Patent number
US06369070B1

Reaction notes

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