Stannous Chloride → Ethyl (2-amino-6-methoxy-phenyl)-carbamate

HRID 33388

Reaction equation

HRID 33388 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-])=O)[C:4]=1[NH:12][C:13](=[O:17])[O:14][CH2:15][CH3:16].Cl[Sn]Cl>CO>[NH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[NH:12][C:13](=[O:17])[O:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 86603972Ethyl (2-methoxy-6-nitrophenyl)carbamate

Product 1

HCID 86603973Ethyl (2-amino-6-methoxy-phenyl)-carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

25.0 g (0.104 mol) ethyl (2-methoxy-6-nitro-phenyl)-carbamate are dissolved in 400 mL methanol. 116.4 g (0.516 mol) SnCl2 2H2O are added and the mixture is refluxed for 3 hours. The reaction mixture is evaporated down, combined with sodium carbonate solution and filtered. The aqueous phase is repeatedly extracted with dichloromethane and the combined organic phases are washed with sodium chloride solution, dried and evaporated down. The residue that crystallises out on standing is stirred with isopropanol. Yield: 13.0 g (59%); mass spectroscopy: [M+H]+=211.

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. customThe reaction mixture is evaporated down
  3. filtrationfiltered
  4. extractionThe aqueous phase is repeatedly extracted with dichloromethane
  5. washthe combined organic phases are washed with sodium chloride solution
  6. customdried
  7. customevaporated down
  8. customThe residue that crystallises out on standing

Sources & evidence

ORD record
ord-0b62773a7e51420fbebb818a281d5476
Source dataset
uspto-grants-2008_09
Patent number
US07429583B2

Linked notes

Loading…