Methanol → 4-Fluoro-N2-pyridin-4-yl-benzene-1,2-diamine

HRID 243099Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of (5-fluoro-2-nitro-phenyl)-pyridin-4-yl-amine (375 mg, 1.61 mmol) in a 3:1 mixture of MeOH:water (40 mL) were added NH4Cl (516 mg, 9.65 mmol) and iron powder (359 mg, 6.43 mmol) and the reaction mixture heated at 80° C. for 2 h. After cooling to RT, the solid was filtered through a pad of Celite® and washed with additional MeOH. The filtrate was concentrated in vacuo and the resulting residue partitioned between DCM and a saturated aqueous solution of NaHCO3. The organic fraction was dried and concentrated in vacuo to afford the title compound as a dark beige solid (215 mg, 66%). LCMS (Method C): RT 1.32 min [M+H]+ 204.09

Workup

temperatureAfter cooling to RT
filtrationthe solid was filtered through a pad of Celite®
washwashed with additional MeOH
concentrationThe filtrate was concentrated in vacuo
customthe resulting residue partitioned between DCM
customThe organic fraction was dried
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e6c3935a8d044fd78e747c523c097daa
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

Loading…