Aniline → 3-nitro-N-phenylpyridin-2-amine
Reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[N+:8]([C:7]1[C:2]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]Participants
Conditions
- Temperature
- 120 °C
Procedure
A mixture of 15 g (0.10 mole) of 2-chloro-3-nitro pyridine and 9.3 g (0.10 mole) of aniline were heated by means of an oil bath at about 120° C. for 30 min. The mass spectra of a sample taken at 15 min indicated presence mainly of the title compound. The product was partitioned between chloroform and aqueous basic solution (sodium hydroxide). The aqueous solution was washed twice more with chloroform. The chloroform extracts were washed once with a sodium chloride-sodium bicarbonate solution, dried over sodium sulfate, filtered and evaporated to give 21.9 g of black oil which solidified on standing. The solid was triturated in 30-60 pet-ether for 1 hr. The remaining solid was filtered off and washed with the same solvent and air dried to give 18.7 g (87%). The solid was recrystallized from cyclohexane. Nuclear magnetic resonance confirmed the title compound, m.p. 172°-174° C.
Sources & evidence
- ORD record
- ord-40907e87eaed498fbab4024af24d9de8
- Source dataset
- uspto-grants-1985_12
- Patent number
- US04558132
Reaction notes
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