Stannous Chloride → 2-Benzyloxy-6-methylaniline

HRID 660828

Reaction equation

HRID 660828 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[N+:16]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[Sn]Cl>CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[NH2:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 33441871-Benzyloxy-3-methyl-2-nitrobenzene

Product 1

HCID 27629472-Benzyloxy-6-methylaniline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 1-benzyloxy-3-methyl-2-nitrobenzene (5.0 g, 20.6 mmol) in EtOAc (150 mL) is added SnCl2 (23.2 g, 103 mmol) and the suspension is heated at 80° C. overnight. The suspension is filtered and the filtrate washed with sat. NaHCO3 and extracted with EtOAc. The combined organic layers are washed with water, brine, then dried over MgSO4 and filtered. The solvent is removed under reduced pressure and the residue is purified by flash chromatography (hexanes/EtOAc=10:1 to 5:1) to give the title compound as a yellow oil.

Workup

  1. filtrationThe suspension is filtered
  2. washthe filtrate washed with sat. NaHCO3
  3. extractionextracted with EtOAc
  4. washThe combined organic layers are washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent is removed under reduced pressure
  8. customthe residue is purified by flash chromatography (hexanes/EtOAc=10:1 to 5:1)

Sources & evidence

ORD record
ord-497302fff055418384eab6c259e66d60
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Linked notes

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