Stannous Chloride → 4-Iodo-3-methoxyaniline

HRID 1403200Notes

Reaction equation

HRID 1403200 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[O:11][CH3:12].Cl[Sn]Cl>C(O)C>[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 2301031-Iodo-2-methoxy-4-nitrobenzene

Product 1

HCID 226370284-Iodo-3-methoxyanilineYield 59.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Iodo-2-methoxy-4-nitro-benzene (6.01 g, 21.54 mmol) in absolute ethanol (127 mL) was cooled with an ice bath and treated with SnCl2 (18.83 g, 99.31 mmol). The bath was removed and the mixture was stirred at room temperature for 4 h then poured into ice (300 mL), stirred and treated carefully with saturated aqueous sodium bicarbonate (250 mL) (pH 7-8). The solid was filtered with suction and the panel washed thoroughly with EtOAc (500 mL and 4×200 mL). The aqueous layer was separated, dried over sodium sulphate and evaporated. Purification of the crude by flash chromatography on silica gel (hexane/EtOAc 1/1) furnished the title compound (3.17 g, 59%).

Workup

  1. customThe bath was removed
  2. additionthen poured into ice (300 mL)
  3. stirringstirred
  4. additiontreated carefully with saturated aqueous sodium bicarbonate (250 mL) (pH 7-8)
  5. filtrationThe solid was filtered with suction
  6. washthe panel washed thoroughly with EtOAc (500 mL and 4×200 mL)
  7. customThe aqueous layer was separated
  8. dry with materialdried over sodium sulphate
  9. customevaporated
  10. customPurification of the crude by flash chromatography on silica gel (hexane/EtOAc 1/1)

Sources & evidence

ORD record
ord-d0986eb6d3bd46d7956bd11b1b83a598
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

Loading…