Sodium Hydroxide → HCID 86662492, compound

HRID 1892035Notes

Reaction equation

HRID 1892035 reaction equation
[CH2:1]([O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[CH:16]=[N:17][OH:18])[CH:2]1O[CH2:3]1.[CH2:19]([O:21][C:22]([CH2:24][CH2:25]CCCOC1C=CC2C(=CC=CC=2)C=1C=O)=[O:23])[CH3:20].[OH-].[Na+].Cl.NO>C(O)C.O>[CH2:19]([O:21][C:22]([CH2:24][CH2:25][CH2:3][CH2:2][CH2:1][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[CH:16]=[N:17][OH:18])=[O:23])[CH3:20]

Participants

7

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 443297Hydroxyamine hydrochloride2×HCID 86662489HCID 86662489, compoundHCID 86662491HCID 86662491, compound

Product 1

HCID 86662492HCID 86662492, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

As shown in Chemical Formula 4, a mixed solution in which 0.206 g (0.654 mmol) of 2-[5-(ethoxycarbonyl)pentyloxy]-1-naphthoaldehyde (6) was dissolved in a solvent mixture of 2 mL of ethanol and 1 mL of water was prepared. Separately, an aqueous solution in which 25.1 mg (0.628 mmol) of sodium hydroxide and 68.7 mg (0.994 mmol) of hydroxylamine hydrochloride were dissolved in 1 mL of water in an ice bath was prepared. This aqueous solution was added to the mixed solution and the resultant reaction mixture was stirred at room temperature for 30 minutes to effect the reaction. However, by the sampling of the reaction mixture, remaining of the raw material was confirmed, so 27.3 mg (0.683 mmol) of sodium hydroxide and 55.8 mg (0.803 mmol) of hydroxylamine hydrochloride were added to the reaction mixture, and the resultant reaction mixture was stirred at room temperature for 1 hour to effect the reaction. The resultant solid was recovered by filtration and the crude product was recrystallized in hexane-EtOH (hexane-ethanol) to obtain 127 mg (yield: 59%) of 2-[5-(ethoxycarbonyl)pentyloxy]-1-naphthoaldehyde oxime (7) as a colorless crystal.

Workup

  1. customwas prepared
  2. customwas prepared
  3. additionThis aqueous solution was added to the mixed solution
  4. customthe resultant reaction mixture
  5. customthe reaction
  6. aliquotHowever, by the sampling of the reaction mixture
  7. customthe resultant reaction mixture
  8. stirringwas stirred at room temperature for 1 hour
  9. customthe reaction
  10. filtrationThe resultant solid was recovered by filtration
  11. customthe crude product was recrystallized in hexane-EtOH (hexane-ethanol)

Sources & evidence

ORD record
ord-21dd164847e44be584bd0cdb6376adf5
Source dataset
uspto-grants-2013_08
Patent number
US08507611B2

Reaction notes

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