Isoamyl Nitrite → HCID 135718523, compound

HRID 1266943Notes

Reaction equation

HRID 1266943 reaction equation
[O-]CC.[Na+].[N:5](OCCC(C)C)=O.[NH2:13][C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=1.[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.O>[CH3:20][C:19]1[C:14]([N:13]=[N:5][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])=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 8053Isoamyl NitriteHCID 86632-NaphtholHCID 153472-Amino-3-methylpyridineHCID 2723922Sodium ethoxide

Product 1

HCID 135718523HCID 135718523, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A reaction flask was loaded with ethanol (25 ml), sodium ethoxide (2.5 g), isopentyl nitrite (4.3 g), and 2-amino-3-methylpyridine (4 g), and they were mixed. The mixture was heated up to the reflux temperature of the solvent with stirring and stirred at the reflux temperature for 3 hours. Then, the heating was stopped and the mixture was cooled to room temperature with stirring. To this, 2-naphthol (3 g) dissolved in ethanol (5 ml) was dropwise added in 1.5 hours. The mixture was heated again and stirred at the reflux temperature for 4 hours. Then, the heating and stirring were stopped and the mixture was left to cool. The reaction mixture was filtrated to remove insoluble components, and the filtrate was condensed. Water was added little by little to the residue for crystallization. The filtrated crystals were put into metanol (20 ml). This was stirred for 30 minutes, followed by recrystallization. The crystals were dried to give intended crystals (1.5 g).

Workup

  1. additionwere mixed
  2. temperatureThe mixture was heated up to the reflux temperature of the solvent
  3. stirringstirred at the reflux temperature for 3 hours
  4. stirringwith stirring
  5. additionwas dropwise added in 1.5 hours
  6. temperatureThe mixture was heated again
  7. stirringstirred at the reflux temperature for 4 hours
  8. stirringThen, the heating and stirring
  9. waitthe mixture was left
  10. temperatureto cool
  11. filtrationThe reaction mixture was filtrated
  12. customto remove insoluble components
  13. customcondensed
  14. customfor crystallization
  15. stirringThis was stirred for 30 minutes
  16. customfollowed by recrystallization
  17. customThe crystals were dried
  18. customto give

Sources & evidence

ORD record
ord-3a191dbc6b4e422baac03ac2527b2687
Source dataset
uspto-grants-2003_04
Patent number
US06551682B1

Reaction notes

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