N-(2,6-dimethyl-4-nitrophenyl)acetamide → N-(4-Amino-2,6-dimethylphenyl)acetamide

Zinc dust (30 g) was added in portions over 10 minutes to N-(2,6-dimethyl-4-nitro-phenyl)-acetamide (5.09 g) in tetrahydrofuran (200 mL) and acetic acid (60 mL) cooled to 0° C. The reaction mixture was filtered after 30 minutes through silica-(50 g), which was washed with methanol/ethyl acetate (20:80, 100 mL). The organic phase was washed with saturated aqueous sodium bicarbonate (100 mL) and treated with heptane until the title compound precipitated, which was collected, washed with heptane and dried in vacuo to furnish 1.20 g (28% yield) of the title compound as a pale red solid. 1H NMR (500 MHz, DMSO-d6): 1.95 (s, 3H), 1.96 (s, 6H), 4.82 (s, 2H), 6.23 (s, 2H), 8.79 (s, 1H).

1. filtrationThe reaction mixture was filtered after 30 minutes through silica-(50 g), which
2. washwas washed with methanol/ethyl acetate (20:80, 100 mL)
3. washThe organic phase was washed with saturated aqueous sodium bicarbonate (100 mL)
4. additiontreated with heptane until the title compound
5. customprecipitated
6. customwhich was collected
7. washwashed with heptane
8. customdried in vacuo

ORD-Eintrag

ord-5ac57eab30874829860177d6fd9412e4

Quelldatensatz

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07601870B2