Water → 5-Chloro-N-(2-nitrophenyl)-2-pyridinamine

HRID 1792511Notes

Reaction equation

HRID 1792511 reaction equation
[OH-].[K+].F[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-:12])=[O:11].[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([NH2:20])=[N:18][CH:19]=1.O>CS(C)=O>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([NH:20][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N+:10]([O-:12])=[O:11])=[N:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 661742-Amino-5-chloropyridineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 220312255-Chloro-N-(2-nitrophenyl)-2-pyridinamineYield 68%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
20 °C

Procedure

9.9 g potassium hydroxide powder and 5.0 g 1-fluoro-2-nitrobenzene were added little by little in this order to a solution of 5.8 g 5-chloro-2-aminopyridine in dimethyl sulfoxide (100 mL), and the mixture was stirred at 20° C. for 4 hours under nitrogen atmosphere. The reaction solution was poured into iced water and extracted with ethyl acetate. The organic layer was washed with water and brine and dried over sodium sulfate. The solvent was evaporated, and the residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) and recrystallized from ethyl acetate/hexane, to give 6.02 g of the title compound as orange crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)
  6. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-9ea422943cb34707b6430d78d4335819
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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