Methanol → N2-(3-Chlorophenyl)-2,3-pyridinediamine

HRID 242986Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:14]([N+:15]([O-])=O)=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.CO.[NH4+].[Cl-]>[Fe].O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:14]([NH2:15])=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of (3-chlorophenyl)-(3-nitropyridin-2-yl)amine (111 mg, 0.45 mmol) in a 3:1 mixture MeOH:water (20 mL) were added NH4Cl (154 mg, 2.88 mmol) and iron powder (107 mg, 1.92 mmol) and the reaction mixture heated at 90° C. for 3 h. After cooling to RT, the solid was filtered through a pad of Celite® and the filtrate concentrated in vacuo. The resulting residue was partitioned between EtOAc and water. The aqueous phase was further extracted with EtOAc (×3) and the combined organic fractions washed with brine, dried (Na2SO4) and concentrated in vacuo. The resulting brown oil was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM) to afford the title compound as a brown solid (29 mg, 30%). LCMS (Method C): RT 1.84 min [M+H]+ 220.1.

Workup

temperatureAfter cooling to RT
filtrationthe solid was filtered through a pad of Celite®
concentrationthe filtrate concentrated in vacuo
customThe resulting residue was partitioned between EtOAc and water
extractionThe aqueous phase was further extracted with EtOAc (×3)
washthe combined organic fractions washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customThe resulting brown oil was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM)

Sources & evidence

ORD record: ord-dab4cb783605429aa8bc29620b0d9c45
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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