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

HRID 1518524Notes

Reaction equation

HRID 1518524 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 was 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. washwas washed 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-a21ffd62742943138f86d767848507cb
Source dataset
uspto-grants-2012_07
Patent number
US08232406B2

Reaction notes

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