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

HRID 1820116Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([CH3:11])[C:3]=1[NH:12][C:13](=[O:15])[CH3:14]>O1CCCC1.C(O)(=O)C.[Zn]>[NH2:8][C:6]1[CH:7]=[C:2]([CH3:1])[C:3]([NH:12][C:13](=[O:15])[CH3:14])=[C:4]([CH3:11])[CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-5ac57eab30874829860177d6fd9412e4
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601870B2

Reaction notes

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