Isoamyl Nitrite → HCID 3995049, compound

HRID 1266914Notes

Reaction equation

HRID 1266914 reaction equation
[Cl:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[O-]CC.[Na+].[N:14](OCCC(C)C)=O.[CH:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][C:23]=1[OH:32]>C(O)C>[Cl:1][C:2]1[C:3]([N:9]=[N:14][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][C:23]=2[OH:32])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 4

HCID 8053Isoamyl NitriteHCID 86632-NaphtholHCID 778863,5-Dichloro-3-pyridylamineHCID 2723922Sodium ethoxide

Product 1

HCID 3995049HCID 3995049, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A reaction flask was loaded with 3,5-dichloro-2-aminopyridine (40 g), ethanol (300 ml), and sodium ethoxide (14 g), followed by dropwise addition of isopentyl nitrite (28 g) to the flask in 30 minutes with stirring. After the dropwise addition was ended, heating was started and the mixture was stirred at 75 to 80° C. for four hours. The heating was stopped, and the reaction mixture was cooled to room temperature, followed by dropwise addition of 2-naphthol (17 g) dissolved in ethanol (50 ml) to the mixture in one hour. The resultant mixture was stirred at room temperature for one hour, heated, and stirred at 75 to 80° C. for three hours, followed by stopping the heating and then leaving the mixture to stand overnight. The reaction mixture was filtrated to remove insoluble components, and the filtrate was condensed by an evaporator. The residue was dissolved in ethyl acetate and, after being successively washed with an aqueous solution of sodium hydroxide and water, the ethyl acetate layer was condensed by an evaporator, followed by addition of methanol to the residue for crystallization. The resultant was filtrated and the crystals were dried to give intended crystals (10 g).

Workup

  1. additionAfter the dropwise addition
  2. temperatureheating
  3. stirringthe mixture was stirred at 75 to 80° C. for four hours
  4. temperatureheated
  5. stirringstirred at 75 to 80° C. for three hours
  6. customthen leaving the mixture
  7. filtrationThe reaction mixture was filtrated
  8. customto remove insoluble components
  9. customcondensed
  10. customby an evaporator
  11. dissolutionThe residue was dissolved in ethyl acetate
  12. washafter being successively washed with an aqueous solution of sodium hydroxide and water
  13. customcondensed
  14. customby an evaporator
  15. additionfollowed by addition of methanol to the residue for crystallization
  16. filtrationThe resultant was filtrated
  17. customthe crystals were dried
  18. customto give

Sources & evidence

ORD record
ord-6d5210fbb07444fb986ce78e8098be08
Source dataset
uspto-grants-2003_04
Patent number
US06551682B1

Reaction notes

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