2-Chloro-3-nitropyridine → HCID 14677546, compound

HRID 330537Notes

Reaction equation

HRID 330537 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:11][C:12]1[CH:13]=[C:14]([CH2:17][NH2:18])[O:15][CH:16]=1.C(=O)([O-])O.[Na+]>C(O)C>[CH3:11][C:12]1[CH:13]=[C:14]([CH2:17][NH:18][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[O:15][CH:16]=1

Participants

5

Reactant 3

HCID 796132-Chloro-3-nitropyridineHCID 516892Sodium BicarbonateHCID 146775454-Methyl-2-furanmethanamine

Product 1

HCID 14677546HCID 14677546, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 10.4 parts of 2-chloro-3-nitropyridine, 8 parts of 4-methyl-2-furanmethanamine, 7.6 parts of sodium hydrogen carbonate and 120 parts of ethanol was stirred overnight at reflux temperature. The reaction mixture was evaporated and the residue was taken up in water. The product was extracted with 1,1'-oxybisethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using trichloromethane as eluent. The pure fractions were collected and the eluent was evaporated, yielding 14.9 parts (91.2%) of N-[(4-methyl-2-furanyl)methyl]-3-nitro-2-pyridinamine as a residue (int. 3).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. extractionThe product was extracted with 1,1'-oxybisethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated

Sources & evidence

ORD record
ord-5453942a16ed458bb7797593304aaba2
Source dataset
uspto-grants-1990_01
Patent number
US04897401

Reaction notes

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