HCID 86628083, compound → 5-(3,4-Dimethoxy-5-nitrophenyl)-3-(2-(trifluoromethyl)pyridin-3-yl)-1,2,4-triazine

HRID 42657Notes

Reaction equation

HRID 42657 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[N:12]=[CH:11][CH:10]=[CH:9][C:4]=1/[C:5](=[N:7]/[NH2:8])/[NH2:6].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([C:28](=O)[CH:29]=O)[CH:20]=[C:21]([N+:25]([O-:27])=[O:26])[C:22]=1[O:23][CH3:24]>C(O)C>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([C:28]2[N:6]=[C:5]([C:4]3[C:3]([C:2]([F:13])([F:1])[F:14])=[N:12][CH:11]=[CH:10][CH:9]=3)[N:7]=[N:8][CH:29]=2)[CH:20]=[C:21]([N+:25]([O-:27])=[O:26])[C:22]=1[O:23][CH3:24]

Participants

4

Reactant 2

HCID 86628083HCID 86628083, compoundHCID 87543466N'-amino-2-(trifluoromethyl)pyridine-3-carboximidamide

Product 1

HCID 687018815-(3,4-Dimethoxy-5-nitrophenyl)-3-(2-(trifluoromethyl)pyridin-3-yl)-1,2,4-triazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of (Z)-2-(trifluoromethyl)nicotinohydrazonamide (1.02 g, 5 mmol) in ethanol (30 mL) was added 2-(3,4-dimethoxy-5-nitrophenyl)-2-oxoacetaldehyde (1.19 g, 5 mmol). The reaction mixture was heated to reflux for 5 hours. It was then cooled to room temperature and the solvent was removed by evaporation. The residue was dissolved in dichloromethane (30 mL) and the organic phase was washed with water and dried over anhydrous magnesium sulphate, filtered and evaporated. The crude product was recrystallized from isopropanol to give 5-(3,4-dimethoxy-5-nitrophenyl)-3-(2-(trifluoromethyl)pyridin-3-yl)-1,2,4-triazine, 1.628 g (80%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 5 hours
  3. customthe solvent was removed by evaporation
  4. dissolutionThe residue was dissolved in dichloromethane (30 mL)
  5. washthe organic phase was washed with water
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was recrystallized from isopropanol

Sources & evidence

ORD record
ord-69bb41e3d1e54a1b9ebe116feed77f24
Source dataset
uspto-grants-2013_09
Patent number
US08536203B2

Reaction notes

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