HCID 22648150, compound → HCID 22647984, compound

HRID 394165Notes

Reaction equation

HRID 394165 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([CH3:15])=[CH:13][C:12]([N+:16]([O-])=O)=[CH:11][N:10]=1>CO.[Ni]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[CH:11][C:12]([NH2:16])=[CH:13][C:14]=1[CH3:15]

Participants

4

Reactant 1

HCID 22648150HCID 22648150, compound

Product 1

HCID 22647984HCID 22647984, compoundYield 96.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 2-(2,4-difluorophenyl)-3-methyl-5-nitropyridine (7.5 g, 30 mmol, 1 eq) in methanol (100 mL) in a 500 mL round bottom flask was added 7 g of Raney Nickel slurry. The flask was evacuated and charged with hydrogen 4 times. The mixture was stirred under H2. After 5 h the reaction flask was purged with nitrogen. The mixture was filtered and the methanol was removed under reduced pressure giving 6.4 g 6-(2,4-difluorophenyl)-5-methylpyridin-3-amine.

Workup

  1. customThe flask was evacuated
  2. additioncharged with hydrogen 4 times
  3. customAfter 5 h the reaction flask was purged with nitrogen
  4. filtrationThe mixture was filtered
  5. customthe methanol was removed under reduced pressure

Sources & evidence

ORD record
ord-9457882e2152474d8a5087c27316b0cd
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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