N-(2,3-difluorophenyl)-3-nitropyridin-4-amine → N4-(2,3-difluorophenyl)pyridine-3,4-diamine

HRID 253970Notes

Reaction equation

HRID 253970 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[N+:16]([O-])=O.[H][H]>CO.[Pd]>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[NH2:16]

Participants

5

Reactant 2

HCID 58180163N-(2,3-difluorophenyl)-3-nitropyridin-4-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 58179850N4-(2,3-difluorophenyl)pyridine-3,4-diamineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-(2,3-difluorophenyl)-3-nitropyridin-4-amine in 200 mL of methanol under an atmosphere of nitrogen was added 10% Pd/C (0.75 g). The atmosphere was replaced with hydrogen gas and the reaction mixture stirred under balloon pressure for 14 hours at RT. The reaction mixture was filtered over Celite which washed with methanol (3×30 mL). The filtrate was concentrated in vacuo to give a brown solid. The crude product was triturated with petroleum ether (3×50 mL) to afford N4-(2,3-difluorophenyl)pyridine-3,4-diamine (4.0 g, 90% yield) as light brown solid; LC-MS: 222.2 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered over Celite which
  2. washwashed with methanol (3×30 mL)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give a brown solid
  5. customThe crude product was triturated with petroleum ether (3×50 mL)

Sources & evidence

ORD record
ord-53b42ee36d8e4ee9b47573e3946157aa
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

Loading…