Stannous Chloride → Ethyl 3-amino-5-bromobenzoate

HRID 269559Notes

Reaction equation

HRID 269559 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([N+:13]([O-])=O)[CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Sn](Cl)Cl>C(O)C>[NH2:13][C:11]1[CH:10]=[C:4]([CH:3]=[C:2]([Br:1])[CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 26966738Ethyl 3-bromo-5-nitrobenzoate

Product 1

HCID 63021768Ethyl 3-amino-5-bromobenzoateYield 92.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 3-bromo-5-nitrobenzoate (4.4 g, 16 mmol) and tin(II) chloride (40 g, 170 mmol) in ethanol (125 ml) was heated at 80° C. for 2 hours. The mixture was cooled to room temperature and the solvent evaporated. The residue was suspended in ethyl acetate (250 ml) and washed with 2M NaOH (2×250 ml). The organic phase was washed with water, dried and evaporated to give the title compound as a yellow solid (3.6 g, 92%)

Workup

  1. customthe solvent evaporated
  2. washwashed with 2M NaOH (2×250 ml)
  3. washThe organic phase was washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-330ae8d050ae46f99368cae8ef93dd31
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Reaction notes

Loading…