Nitric Acid → N-(4-Methoxy-2-methyl-5-nitrophenyl)acetamide

HRID 634739

Reaction equation

[Sn](Cl)(Cl)(Cl)Cl.[N+:6]([O-:9])(O)=[O:7].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[C:14]([CH3:22])[CH:13]=1>C(Cl)Cl>[CH3:10][O:11][C:12]1[C:17]([N+:6]([O-:9])=[O:7])=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[C:14]([CH3:22])[CH:13]=1

Participants

Conditions

Temperature: -30 °C

Procedure

A mixture of tin(IV)chloride (1 9.3 ml) and 69.5% nitric acid (10.3 ml) in methylene chloride (140 ml) was added dropwise to a solution of N-(4-methoxy-2-methylphenyl)acetamide (28 g, 0.14 mol) in methylene chloride (500 ml) cooled to and maintained at −30° C. The reaction mixture was stirred at −30° C. for 1.5 hours, allowed to warm to ambient temperature then poured on to ice/water. The organic layer was separated and the aqueous layer extracted with ethyl acetate. The combined extracts were dried (MgSO4), the solvent removed by evaporation and the residue purified by column chromatography eluting with petroleum ether/ethyl acetate (2/8) to give N-(4-methoxy-2-methyl-5-nitrophenyl)acetamide (1 7.8 g, 51%)

Workup

temperaturecooled to and
temperatureto warm to ambient temperature
customThe organic layer was separated
extractionthe aqueous layer extracted with ethyl acetate
dry with materialThe combined extracts were dried (MgSO4)
customthe solvent removed by evaporation
customthe residue purified by column chromatography
washeluting with petroleum ether/ethyl acetate (2/8)

Sources & evidence

ORD record: ord-011c050cf513429c849dbcb76c2debdc
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06184225B2

Linked notes

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