Sodium Hydroxide → 3-Methoxybenzene-1,2-diamine

Tin(II) chloride dihydrate (11.9 g, 52.6 mmol) was added to a solution of the above dinitroanisole (2.21 g, 8.76 mmol) in EtOAc (30 mL). The mixture was heated to reflux for 0.25 h upon which the solution became red in color. The solution was cooled to room temperature and poured into aqueous 2.0 M NaOH. The aqueous phase was extracted with EtOAc and the combined organic layers were washed with saturated aqueous NaHCO3. The organic layers were dried over sodium sulfate, eluted through a plug of silica gel (1% ammonium hydroxide in methylene chloride), and the filtrate was concentrated. The residue was dissolved in diethyl ether and extracted (3×) with 1.0 M HCl. The pH of the combined aqueous layers was adjusted to pH=12 with 2.0 M NaOH and extracted with methylene chloride. The combined organic layers were dried over sodium sulfate, filtered and concentrated to provide diaminoanisole (860 mg, 52%) as a red oil.

1. temperatureThe mixture was heated
2. temperatureto reflux for 0.25 h upon which the solution
3. extractionThe aqueous phase was extracted with EtOAc
4. washthe combined organic layers were washed with saturated aqueous NaHCO3
5. dry with materialThe organic layers were dried over sodium sulfate
6. washeluted through a plug of silica gel (1% ammonium hydroxide in methylene chloride)
7. concentrationthe filtrate was concentrated
8. dissolutionThe residue was dissolved in diethyl ether
9. extractionextracted (3×) with 1.0 M HCl
10. extractionextracted with methylene chloride
11. dry with materialThe combined organic layers were dried over sodium sulfate
12. filtrationfiltered
13. concentrationconcentrated

ORD record

ord-86beec9a477543d68be5dd427a600c6b

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07592332B2