N,N-Dimethylaniline → 3-benzyloxy-2-nitro-N-methoxyacetyl-N-methylaniline

HRID 2287574Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:10]([N+:17]([O-:19])=[O:18])=[C:11]([CH:14]=[CH:15][CH:16]=1)[NH:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C1C=CC=CC=1.[CH3:29][O:30][CH2:31][C:32](Cl)=[O:33]>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[C:10]([N+:17]([O-:19])=[O:18])=[C:11]([CH:14]=[CH:15][CH:16]=1)[N:12]([C:32](=[O:33])[CH2:31][O:30][CH3:29])[CH3:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of 3-benzyloxy-2-nitro-N-methylaniline (400 mg) and N,N-dimethylaniline (1 ml) was added methoxyacetyl chloride (310 μl) under nitrogen atmosphere, and the mixture was stirred for 2.5 hours at 90° C. After cooling, ethyl acetate was added to the reaction mixture, and the mixture was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=2:1, v/v) to give 3-benzyloxy-2-nitro-N-methoxyacetyl-N-methylaniline (474.2 mg).

Workup

temperatureAfter cooling
washthe mixture was washed with water and brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was purified by silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record: ord-8934cc7c7c0d4ea08382fd477c733974
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06083961

Reaction notes

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