Stannous chloride dihydrate → 3-Chloro-5-methylaniline

An ethanol solution (75 mL) containing 1-chloro-3-methyl-5-nitro-benzene (5.0 g, 29 mmol) were mixed with SnCl2.2H2O (32.8 g, 146 mmol). The reaction mixture was refluxed for 3.0 h. The solution was concentrated under vacuum, and the residue was re-dissolved in aqueous NaOH, filtered, and extracted with EtOAc. The organic layer was collected, washed with brine, dried over MgSO4(s), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give 3-chloro-5-methyl-phenylamine (4.0 g) as light yellow solids in 97% yield: 1H NMR (500 MHz, CDCl3) δ 6.56 (s, 1 H), 6.48 (s, 1 H), 6.36 (s, 1), 3.66 (s, 2 H), 2.23 (s, 3 H); ESI-MS: m/z 141.7 (M+H)+.

1. temperatureThe reaction mixture was refluxed for 3.0 h
2. concentrationThe solution was concentrated under vacuum
3. dissolutionthe residue was re-dissolved in aqueous NaOH
4. filtrationfiltered
5. extractionextracted with EtOAc
6. customThe organic layer was collected
7. washwashed with brine
8. dry with materialdried over MgSO4(s)
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by column chromatography on silica gel

ORD record

ord-1791404cd9314ce89afb7c5561301ec3

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08999983B2