Dimethylformamide → N-[(4-chlorophenyl)methyl]-3-nitropyridin-2-amine

HRID 55498Notes

Reaction equation

HRID 55498 reaction equation
O[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.S(Cl)(Cl)=O.CN(C)C=O.[Cl:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH2:26])=[CH:23][CH:22]=1>C1(C)C=CC=CC=1>[Cl:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH:26][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 660364-ChlorobenzylamineHCID 178526677HCID 178526677, compound

Product 1

HCID 2800352N-[(4-chlorophenyl)methyl]-3-nitropyridin-2-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 10.3 g of 2-hydroxy-3-nitropyridine and 25.5 ml of thionyl chloride was heated under reflux for 2.5 hours, after which 1.1 ml of dimethylformamide were rapidly added to the mixture, which was then heated under reflux for 2.5 hours. At the end of this time, the reaction mixture was freed from the solvent by evaporation under reduced pressure. 80 ml of toluene and 19.1 g of sodium carbonate were added to the residue thus obtained, and then a solution of 12.3 ml of 4-chlorobenzylamine in 20 ml of toluene was added dropwise to the resulting mixture, which was then stirred at 85° C. for 4 hours. At the end of this time, the insoluble material in the reaction mixture was removed by filtration. The filtrate was washed with water and dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure. The resulting residue was crystallized by trituration with 2-propanol, to give 12.0 g of the title compound, melting at 95°-96° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2.5 hours
  3. temperaturewas then heated
  4. temperatureunder reflux for 2.5 hours
  5. customAt the end of this time, the reaction mixture was freed from the solvent by evaporation under reduced pressure
  6. addition80 ml of toluene and 19.1 g of sodium carbonate were added to the residue
  7. customthus obtained
  8. customAt the end of this time, the insoluble material in the reaction mixture was removed by filtration
  9. washThe filtrate was washed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. customafter which the solvent was removed by distillation under reduced pressure
  12. customThe resulting residue was crystallized by trituration with 2-propanol

Sources & evidence

ORD record
ord-534a5452e3d1451ca980900efc33a77e
Source dataset
uspto-grants-1997_04
Patent number
US05624935

Reaction notes

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