Isoamyl Nitrite → HCID 135718521, compound

HRID 1266940Notes

Reaction equation

HRID 1266940 reaction equation
CC[O-].[Na+].[NH2:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][N:7]=1.[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>[CH3:13][O:12][C:11]1[C:6]([N:5]=[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:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 8053Isoamyl NitriteHCID 86632-NaphtholHCID 2723922Sodium ethoxideHCID 99203842-Amino-3-methoxypyridine

Product 1

HCID 135718521HCID 135718521, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Next, a reaction flask was loaded with sodium ethylate (2.2 g) and ethanol (33 ml) and they were mixed. To the mixture, 2-amino-3-methoxypyridine (3.3 g) was added, and then isopentyl nitrite (3.7 g) was dropwise added in ten minutes with stirring. This was heated and stirred at the reflux temperature for 3.5 hours. The heating was stopped, and the mixture was cooled to room temperature. To this, 2-naphthol (2.7 g) dissolved in ethanol (5 ml) was dropwise added in 30 minutes. After stirring at room temperature for one hour, this mixture was heated to the reflux temperature, followed by stirring for additional 3 hours. The reaction mixture was filtrated and the filtrated crystals were recrystallized with methanol-water and further recrystallized with dioxane to give intended crystals (0.68 g).

Workup

  1. additionwere mixed
  2. temperatureThis was heated
  3. stirringstirred at the reflux temperature for 3.5 hours
  4. additionwas dropwise added in 30 minutes
  5. stirringAfter stirring at room temperature for one hour
  6. temperaturethis mixture was heated to the reflux temperature
  7. stirringby stirring for additional 3 hours
  8. filtrationThe reaction mixture was filtrated
  9. customthe filtrated crystals were recrystallized with methanol-water
  10. customfurther recrystallized with dioxane
  11. customto give

Sources & evidence

ORD record
ord-bb1662aeb49e45d6857af93401aac79e
Source dataset
uspto-grants-2003_04
Patent number
US06551682B1

Reaction notes

Loading…