Isoamyl Nitrite → HCID 135718525, compound

HRID 1266942Notes

Reaction equation

HRID 1266942 reaction equation
CC[O-].[Na+].[NH2:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][CH3:15])=[CH:10][CH:9]=[CH:8][N:7]=1.[N:16](OCCC(C)C)=O.[CH:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][C:25]=1[OH:34]>C(O)C>[CH2:13]([O:12][C:11]1[C:6]([N:5]=[N:16][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=[CH:26][C:25]=2[OH:34])=[N:7][CH:8]=[CH:9][CH:10]=1)[CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 8053Isoamyl NitriteHCID 86632-NaphtholHCID 2723922Sodium ethoxideHCID 14676218HCID 14676218, compound

Product 1

HCID 135718525HCID 135718525, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Next, a flask was loaded with sodium ethylate (1.6 g), ethanol (14 ml), and 2-amino-3-propoxypyridine (3.8 g), and they were mixed. To the mixture, isopentyl nitrite (2.7 g) was dropwise added in 20 minutes with stirring. This was stirred at the reflux temperature for 4 hours, and then cooled to room temperature. Thereafter, to this, 2-naphthol (2.0 g) dissolved in ethanol (5 ml) was dropwise added in one hour. After stirring at room temperature for two hours, this mixture was heated to the reflux temperature, followed by stirring for additional 2 hours. The reaction mixture was filtrated and the filtrate was condensed to precipitate crystals. The crystals were filtrated for collection and recrystallized with dioxane-water to give intended crystals (0.59 g).

Workup

  1. additionwere mixed
  2. stirringThis was stirred at the reflux temperature for 4 hours
  3. additionwas dropwise added in one hour
  4. stirringAfter stirring at room temperature for two hours
  5. temperaturethis mixture was heated to the reflux temperature
  6. stirringby stirring for additional 2 hours
  7. filtrationThe reaction mixture was filtrated
  8. customcondensed
  9. customto precipitate crystals
  10. filtrationThe crystals were filtrated for collection
  11. customrecrystallized with dioxane-water
  12. customto give

Sources & evidence

ORD record
ord-bcc37bbd64684155ad97be7a188f1593
Source dataset
uspto-grants-2003_04
Patent number
US06551682B1

Reaction notes

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