Stannous chloride dihydrate → tert-Butyl [1-(3-aminophenyl)ethyl]carbamate

HRID 840592Notes

Reaction equation

HRID 840592 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH3:19])[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][CH:9]([CH3:19])[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 22620027HCID 22620027, compound

Product 1

HCID 16740730tert-Butyl [1-(3-aminophenyl)ethyl]carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the N-t-butyloxycarbonyl-3-nitro-α-methylbenzylamine (1.79 g, 6.74 mmol) in dimethylformamide (50 1 mL) was added tin(II) chloride dihydrate (9.12 g, 40.4 mmol) and the reaction was stirred at room temperature for 48 hours. The dimethylformamide was removed under vacuum, residue resuspended in dichloromethane (100 ml), washed with brine (100 mL), filtered through a celite pad, and solvent removed to provide the crude aniline.

Workup

  1. customThe dimethylformamide was removed under vacuum, residue
  2. washwashed with brine (100 mL)
  3. filtrationfiltered through a celite pad, and solvent
  4. customremoved

Sources & evidence

ORD record
ord-9a568b77a8f2471ab131dc21e2c1aa0c
Source dataset
uspto-grants-2002_04
Patent number
US06369070B1

Reaction notes

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