Stannous Chloride → 2-Benzyloxy-6-methylaniline

HRID 1642648Notes

Reaction equation

HRID 1642648 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
60 °C

Procedure

To a 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 mixture is heated at 60° C. for 72 h. The mixture is then filtered and to the filtrate is added saturated NaHCO3 and solid Na2CO3. It is then filtered again. EtOAc layer is separated and washed with brine, dried and concentrated. The residue is purified by flash chromatography to give the title compound as a yellow oil.

Workup

  1. filtrationThe mixture is then filtered and to the filtrate
  2. additionis added saturated NaHCO3 and solid Na2CO3
  3. filtrationIt is then filtered again
  4. customEtOAc layer is separated
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-454991d3aa234314a90202bd809bf9c1
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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