Hydrochloric Acid → 1-(1,4-Dimethoxynaphthalen-2-yl)-propane-1,2-dione 2-oxime

HRID 1790291Notes

Reaction equation

HRID 1790291 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[C:15](=[O:18])[CH2:16][CH3:17].Cl.[N:20](OCCCC)=[O:21]>C(OCC)C>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[C:15](=[O:18])[C:16](=[N:20][OH:21])[CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 10996Butyl nitrite2×HCID 22041763HCID 22041763, compound

Product 1

HCID 865927571-(1,4-Dimethoxynaphthalen-2-yl)-propane-1,2-dione 2-oximeYield 55.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The product from Step A (1.28 g, 5.24 mmol) was dissolved in ethyl ether (50 mL), anhydrous hydrogen chloride gas was added through this solution at moderate rate for 5 min. Butyl nitrite (0.68 mL, 5.77 mmol) was then added dropwise. Hydrogen chloride bubbling was continued for an additional 10 min. after addition of butyl nitrite was completed, the reaction mixture was then stirred at room temperature for 4 hr. The volatiles were removed by evaporation under vacuum and the residue was purified by flash chromatography (silica gel, ethyl acetate/hexane: 0.5/9.5) to give an oil (0.8 g): MS 274 (M+1).

Workup

  1. customThe volatiles were removed by evaporation under vacuum
  2. customthe residue was purified by flash chromatography (silica gel, ethyl acetate/hexane: 0.5/9.5)

Sources & evidence

ORD record
ord-6ac4fd3e3c5d4e6bace153926c2ac20d
Source dataset
uspto-grants-2006_07
Patent number
US07071225B2

Reaction notes

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