N-Methyl-3-nitro-5-(trifluoromethyl)pyridin-2-amine → N2-Methyl-5-(trifluoromethyl)pyridine-2,3-diamine

HRID 533655Notes

Reaction equation

HRID 533655 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][C:6]([C:12]([F:15])([F:14])[F:13])=[CH:5][N:4]=1.[H][H]>[C].[Pd].C(O)C>[CH3:1][NH:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([C:12]([F:15])([F:13])[F:14])=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 2775319N-Methyl-3-nitro-5-(trifluoromethyl)pyridin-2-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 2735930N2-Methyl-5-(trifluoromethyl)pyridine-2,3-diamineYield 83.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-methyl-(3-nitro-5-trifluoromethyl-pyridin-2-yl)-amine (6.93 g), 5% of palladium-carbon (0.69 g), and ethanol was stirred under about 1 atm of hydrogen at room temperature for 10 hours. The reaction mixture was filtered through Celite®, and then the filtrate was concentrated under reduced pressure to give 5.02 g of N2-methyl-5-trifluoromethylpyridin-2,3-diamine (Compound (1F)-1).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4e2fb92a64fe4c21aa8d9a761ed94fa7
Source dataset
uspto-grants-2014_10
Patent number
US08853238B2

Reaction notes

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