Stannous chloride dihydrate → 2-Methoxy-p-toluidine

To a solution of 2-methoxy-4-methyl-1-nitrobenzene (5 g; 29.9 mmol) in methanol (200 mL) was added Tin(II) chloride dihydrate (33.7 g; 150 mmol) and the mixture was heated to reflux for 3 h. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate. A saturated solution of sodium hydrogen carbonate was added until pH 8. A suspension formed and the mixture was filtered on a plug of celite. The organic phase was separated, washed with a saturated solution of sodium hydrogen carbonate solution and dried over magnesium sulphate. The solvent was removed under reduced pressure and the residue was used as such in the next reaction.

1. temperaturethe mixture was heated
2. temperatureto reflux for 3 h
3. customThe solvent was removed under reduced pressure
4. dissolutionthe residue was dissolved in ethyl acetate
5. additionA saturated solution of sodium hydrogen carbonate was added until pH 8
6. customA suspension formed
7. filtrationthe mixture was filtered on a plug of celite
8. customThe organic phase was separated
9. washwashed with a saturated solution of sodium hydrogen carbonate solution
10. dry with materialdried over magnesium sulphate
11. customThe solvent was removed under reduced pressure
12. customsuch in the next reaction

ORD record

ord-4e7da7b975604ea19ddf5430a9dfeb26

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08906906B2