4-(Pyridin-3-yl)-2-nitroaniline → HCID 10241519, compound
Reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=[CH:6][C:5]=1[NH2:16])([O-])=O>[Pd].C(O)C.CC(=O)OCC>[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:8]2[CH:9]=[C:4]([NH2:1])[C:5]([NH2:16])=[CH:6][CH:7]=2)[CH:11]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
4-Amino-3-nitrophenylboronic acid pinacol ester (1.60 g, 6.06 mmol), 3-bromopyridine (1.10 g, 6.96 mmol), cesium carbonate (3.33 g, 10.22 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride DCM complex (491 mg, 0.60 mmol) were suspended in dimethylformamide (20 mL). The solution was degassed by vacuum several times and placed in an argon atmosphere. It was then heated to 65° C. for 6 hr. After cooling, EA (100 mL) and water (40 mL) were added. When additional water (50 mL) was added to the organic layer, a precipitate was formed in the separatory funnel. The biphasic solution was filtered, and the filtrate was transferred to the separatory funnel and separated. The organic phase was washed twice with water (50 mL each), then with brine, and then dried with sodium sulfate and concentrated under reduced pressure to give 2-nitro-4-(pyridin-3-yl)benzenamine (1.18 g). 2-Nitro-4-(pyridin-3-yl)benzenamine (700 mg, 3.26 mmol) in 1:1 ethanol/EA (40 mL) was hydrogenated at atmospheric pressure with 10% palladium on carbon (90 mg, 0.08 mmol) at room temperature for 2 days. Filtration and concentration under reduced pressure gave 4-(pyridin-3-yl)-benzene-1,2-diamine (621 mg).
Workup
- filtrationFiltration and concentration under reduced pressure
Sources & evidence
- ORD record
- ord-d2dd2af1d3874085ba66f695a76156ce
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129396B2
Reaction notes
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