Aniline → 3-nitro-N-phenylpyridin-2-amine

HRID 242796Notes

Reaction equation

Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:11]1([NH2:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CCN(CC)CC>CN1C(=O)CCC1>[N+:8]([C:7]1[C:2]([NH:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-chloro-3-nitropyridine (3.49 g, 22.0 mmol), phenylamine (2 mL, 22.0 mmol) and Et3N (3.1 mL, 22.0 mmol) in NMP (7 mL) was stirred at 100° C. for 1.5 h under a nitrogen atmosphere. Additional amounts of Et3N (0.2 mL) and of phenylamine (0.1 mL) were added and the stirring was continued for further 30 min. The mixture was then partitioned between EtOAc and water. The aqueous phase was further extracted with EtOAc and the combined organic layers were washed with brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 10-100% DCM in pentane) affording (3-Nitropyridin-2-yl)phenylamine as a red crystalline solid (2.49 g, 58%). LCMS: RT 3.53 min [M+H]+ 216.0.

Workup

waitthe stirring was continued for further 30 min
customThe mixture was then partitioned between EtOAc and water
extractionThe aqueous phase was further extracted with EtOAc
washthe combined organic layers were washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customThe resulting residue was purified by column chromatography (Si—PCC, gradient 10-100% DCM in pentane)

Sources & evidence

ORD record: ord-3ce6f692e56646fc933a88d059878842
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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