2-(2-Chloro-4-fluorophenyl)-3-methyl-5-nitropyridine → 6-(2-Chloro-4-fluorophenyl)-5-methylpyridin-3-amine

HRID 394174Notes

Reaction equation

HRID 394174 reaction equation
[Cl: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>[Ni].CO.CO>[Cl: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 226479942-(2-Chloro-4-fluorophenyl)-3-methyl-5-nitropyridine

Product 1

HCID 226481546-(2-Chloro-4-fluorophenyl)-5-methylpyridin-3-amine

Reagents, catalysts & solvents 2

HCID 22477019Nickel monomethoxideCatalystHCID 887MethanolSolvent

Procedure

A 250 mL round bottom flask was charged with 2-(2-chloro-4-fluorophenyl)-3-methyl-5-nitropyridine (4 g) and methanol (50 mL). To the flask was added Raney nickel/methanol slurry (approx 4 g). The flask was evacuated and charged with hydrogen several times. The mixture was stirred under a balloon of hydrogen for 2.5 h. The flask was purged with nitrogen. The catalyst was filtered off and the filtrate was concentrated under reduced pressure giving 6-(2-chloro-4-fluorophenyl)-5-methylpyridin-3-amine as an off white solid. Mass spectrum (EST) 237 (M+1).

Workup

  1. customThe flask was evacuated
  2. additioncharged with hydrogen several times
  3. customThe flask was purged with nitrogen
  4. filtrationThe catalyst was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fa1e18fe8b434a2daf01a9b5e4b920b4
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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