(5-Fluoro-2-nitrophenyl)pyridin-3-ylamine → 4-Fluoro-N2-pyridin-3-ylbenzene-1,2-diamine

HRID 243166Notes

Reaction equation

HRID 243166 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:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:7]=1>CCOC(C)=O.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[C:5]([NH2:15])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 58459332(5-Fluoro-2-nitrophenyl)pyridin-3-ylamine

Product 1

HCID 584592164-Fluoro-N2-pyridin-3-ylbenzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of (5-fluoro-2-nitrophenyl)pyridin-3-ylamine (2.21 g, 9.5 mmol) in EtOAc (65 mL) was added to a slurry of palladium on carbon (10% by wt, 220 mg) in EtOAc (10 mL) under N2. The reaction mixture was stirred at RT under an atmosphere of hydrogen for 16 h. The mixture was filtered through Celite® and the filtrate concentrated in vacuo to give the title compound as a white solid that turned red upon standing (1.83 mg, 95%). LCMS (Method B): RT 0.81 min [M+H]+ 204. 1H NMR (CDCl3, 400 MHz): δ 8.23 (1H, dd, J=3.0, 1.0 Hz), 8.13 (1H, dd, J=4.5 1.5 Hz), 7.15 (1H, ddd, J=8.0, 4.5, 0.5 Hz), 7.10 (1H, ddd, J=8.5, 2.5, 1.5 Hz), 6.85 (1H, dd, J=9.5, 2.5 Hz), 6.76-6.68 (2H, m), 5.50 (1H, bs), 3.56 (2H, bs).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-fc4e1158587d4a20a1de4ea3b42a142b
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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