2-Ethyl-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-3-nitro-pyridine → 2-Ethyl-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-ylamine

HRID 1354243Notes

Reaction equation

HRID 1354243 reaction equation
[CH2:1]([C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][C:6]([CH3:12])=[C:5]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][C:14]=2[O:24][CH3:25])[N:4]=1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([C:3]1[C:8]([NH2:9])=[CH:7][C:6]([CH3:12])=[C:5]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:22])([F:23])[F:21])=[CH:15][C:14]=2[O:24][CH3:25])[N:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 211047882-Ethyl-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-3-nitro-pyridine

Product 1

HCID 211047912-Ethyl-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Pd/C (0.1 g) is added to a solution of 2-ethyl-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-3-nitro-pyridine (0.3 g, 0.84 mmol) in ethanol (10 mL). The mixture is hydrogenated at a pressure of 50 psi for 4 hours. The mixture is filtered through celite and evaporated to dryness under reduced pressure to give 2-ethyl-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-ylamine as a yellow solid which is used without further purification TLC Rf 0.30 (elution with 5% methanol-methylene chloride).

Workup

  1. filtrationThe mixture is filtered through celite
  2. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-3791917f8bf84495b2772f9d83d9ad90
Source dataset
uspto-grants-2007_05
Patent number
US07223778B2

Reaction notes

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