Isoamyl Nitrite → 112828-31-6

HRID 1266910Notes

Reaction equation

HRID 1266910 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.[O-]CC.[Na+].[N:13](OCCC(C)C)=O.[CH:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][C:22]=1[OH:31]>C(O)C>[CH3:8][C:4]1[N:3]=[C:2]([N:1]=[N:13][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=[CH:23][C:22]=2[OH:31])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 8053Isoamyl NitriteHCID 86632-NaphtholHCID 157652-Amino-6-methylpyridineHCID 2723922Sodium ethoxide

Product 1

HCID 135718511112828-31-6

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A reaction flask equipped with a cooling tube and a stirrer was loaded with 2-amino-6-methylpyridine (50 g), ethanol (250 ml), and sodium ethoxide (9.4 g), followed by dropwise addition of isopentyl nitrite (54 g) to the flask in 30 minutes with stirring. The resultant mixture was heated and further stirred at 75 to 80° C. for 4 hours for reaction. Thereafter, the heating was stopped, and the reaction mixture was cooled to room temperature, followed by dropwise addition of 2-naphthol (33.0 g) dissolved in ethanol (50 ml) in 30 minutes to the mixture. The resultant mixture was stirred at room temperature for one hour, heated, and stirred at 75 to 80° C. for additional two 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 for solidification. The resultant was dissolved in ethyl acetate (500 ml) and, after being successively washed with an aqueous solution of sodium hydroxide and water, the ethyl acetate layer (phase) 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 red orange crystals (2.1 g).

Workup

  1. customA reaction flask equipped with a cooling tube and a stirrer
  2. stirringfurther stirred at 75 to 80° C. for 4 hours for reaction
  3. temperatureheated
  4. stirringstirred at 75 to 80° C. for additional two hours
  5. customthen leaving the mixture
  6. filtrationThe reaction mixture was filtrated
  7. customto remove insoluble components
  8. customcondensed
  9. customby an evaporator for solidification
  10. dissolutionThe resultant was dissolved in ethyl acetate (500 ml)
  11. washafter being successively washed with an aqueous solution of sodium hydroxide and water
  12. customcondensed
  13. customby an evaporator
  14. additionfollowed by addition of methanol to the residue for crystallization
  15. filtrationThe resultant was filtrated
  16. customthe crystals were dried
  17. customto give

Sources & evidence

ORD record
ord-8605d4b68e5b45c29ba2726363507ce2
Source dataset
uspto-grants-2003_04
Patent number
US06551682B1

Reaction notes

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