N,N-Dimethylaniline → 2-Butyrylamino-4-methyl-3-nitropyridine

HRID 1586789

Reaction equation

[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[CH:5]=[CH:4][N:3]=1.CN(C)C1C=CC=CC=1.[C:21](Cl)(=[O:25])[CH2:22][CH2:23][CH3:24]>C(OCC)(=O)C>[C:21]([NH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[CH:5]=[CH:4][N:3]=1)(=[O:25])[CH2:22][CH2:23][CH3:24]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-amino-4-methyl-3-nitropyridine (5.0 g) and N,N-dimethylaniline (8.5 ml) was heated at 100° C. under nitrogen atmosphere. To the solution was added butyryl chloride (3.5 ml) and the mixture was stirred at 100° C. for 5 hours. After being cooled to room temperature, ethyl acetate was added to the reaction mixture. The organic layer was separated and washed successively with water and brine. The solution was dried over magnesium sulfate and the solvent was evaporated in vacuo. The residue was washed with n-hexane to give 2-butyrylamino-4-methyl-3-nitropyridine (7.0 g).

Workup

temperatureAfter being cooled to room temperature
customThe organic layer was separated
washwashed successively with water and brine
dry with materialThe solution was dried over magnesium sulfate
customthe solvent was evaporated in vacuo
washThe residue was washed with n-hexane

Sources & evidence

ORD record: ord-c713399dc6584bccab1178e0da344317
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05215994

Linked notes

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