Aniline → 4-(6-Phenylamino-pyridazin-3-yl)-phenol

HRID 1993361Notes

Reaction equation

Cl[C:2]1[N:7]=[N:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CS(C)=O.C(O)(C(F)(F)F)=O.CCOC(C)=O>[C:16]1([NH:15][C:2]2[N:7]=[N:6][C:5]([C:8]3[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=3)=[CH:4][CH:3]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-(6-chloro-pyridazin-3-yl)-phenol (Step 2, 1 g, 4.84 mmol) and aniline (1.35 g, 14.52 mmol) in 20 mL of DMSO was added 5 drops of TFA. The reaction was heated to 80° C. for 16 h. The solution was cooled to RT and diluted with 100 mL of EtOAc. The organic phase was washed with 40 mL of water, 40 mL of brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography (50% EtOAc/hexane to EtOAc) to give the title compound as a white solid. MS (ESI pos. ion) m/z: 264.2(M+H). Calc'd Exact Mass for C16H13N3O: 263.29.

Workup

temperatureThe solution was cooled to RT
washThe organic phase was washed with 40 mL of water, 40 mL of brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by chromatography (50% EtOAc/hexane to EtOAc)

Sources & evidence

ORD record: ord-7d76ecddf57442f59ad503b84c87144d
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652009B2

Reaction notes

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