2-Chloro-3-nitropyridine → N-(4-Methylphenyl)-3-nitropyridin-2-amine

HRID 1887987Notes

Reaction equation

Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C1(C)C=CC=C[C:12]=1[C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1.C(N(C(C)C)CC)(C)C>O1CCOCC1.C(OCC)(=O)C>[N+:8]([C:7]1[C:2]([NH:21][C:20]2[CH:22]=[CH:23][C:17]([CH3:12])=[CH:18][CH:19]=2)=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 80 °C

Procedure

2-chloro-3-nitropyridine (100 mg, 0.63 mmol) was dissolved in dioxane (4 mL) in a round bottom flask to which p-tolylaniline (68 mg, 0.63 mmol) was added followed by addition of diisopropylethylamine (0.22 mL). The reaction mixture was heated to 80° C. for 24 hours and stopped when complete as observed by LCMS. After cooling to room temperature, the solvent was removed under reduced pressure to afford an oily residue. The residue was dissolved in ethyl acetate (20 mL) and washed with water and brine (5 mL each respectively). The organic phase was separated and dried over Na2SO4. After filtration the solvent was removed under reduced pressure. The crude product was carried on to the next step without further purification. LCMS [M+H]: 230.

Workup

additionwas added
temperatureAfter cooling to room temperature
customthe solvent was removed under reduced pressure
customto afford an oily residue
washwashed with water and brine (5 mL each respectively)
customThe organic phase was separated
dry with materialdried over Na2SO4
filtrationAfter filtration the solvent
customwas removed under reduced pressure
customThe crude product was carried on to the next step without further purification

Sources & evidence

ORD record: ord-80c450600656478ab50c11292e3a316f
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501770B2

Reaction notes

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