Methanol → 3-Methoxy-5-(thiophen-3-yl)aniline

To a mixture of 3-(3-methoxy-5-nitro-phenyl)-thiophene (3.78 g, 16.07 mmol), zinc dust (10.72 g, 160.7 mmol), and ammonium chloride (12.89 g, 241.1 mmol) were added methanol (50 mL) and water (25 mL) at room temperature. After addition of water, the reaction became exothermic. The suspension was stirred for 1 h and the reaction mixture was filtered through the Celite. The filter cake was washed with water and methanol. The filtrate was concentrated to remove methanol and the residue was extracted with ethyl acetate (2×100 mL). The combined extracts were washed with brine solution (100 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was then purified by using an ISCO 120 g column, eluting with 0-20% ethyl acetate in hexanes to afford 3-methoxy-5-thiophen-3-yl-phenylamine (3.08 g, 93%) as a light yellow solid: ES(+)-HRMS m/e calculated for C11H11NOS (M+H)+ 206.0634, found 206.0634.

1. filtrationthe reaction mixture was filtered through the Celite
2. washThe filter cake was washed with water and methanol
3. concentrationThe filtrate was concentrated
4. customto remove methanol
5. extractionthe residue was extracted with ethyl acetate (2×100 mL)
6. washThe combined extracts were washed with brine solution (100 mL)
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe residue was then purified
11. washeluting with 0-20% ethyl acetate in hexanes

ORD record

ord-38df7cac980b454aab72ad20fe635533

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08093385B2