Ethyl Acetate → HCID 67309687, compound

HRID 2383337Notes

Reaction equation

HRID 2383337 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]#[N:13])[CH:3]=1.Cl.[NH2:15][OH:16].C(=O)([O-])[O-].[K+].[K+].[C:23]([O:26][CH2:27][CH3:28])(=[O:25])[CH3:24]>C(O)(C)(C)C.O>[CH2:27]([O:26][C:23]([C:24]1[O:16][N:15]=[C:12]([C:4]2[CH:3]=[C:2]([OH:1])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=2)[N:13]=1)=[O:25])[CH3:28]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochloride2×HCID 534856954-Hydroxynaphthalene-2-carbonitrile

Product 1

HCID 67309687HCID 67309687, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A mixed solution of 4-hydroxynaphthalene-2-carbonitrile (0.34 g), hydroxylamine hydrochloride (0.14 g) and potassium carbonate (0.30 g) in tert-butylalcohol (4.5 mL) and water (0.5 mL) was stirred at 80° C. for 6 hours. To the reaction mixture was added hydroxylamine hydrochloride (0.14 g), and the mixture was stirred at room temperature for 1 hour. The reaction solution was diluted with ethyl acetate, and washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol). This compound (0.22 g) was dissolved in dichloromethane (5.3 mL). To the mixture were added ethyl oxalyl chloride (0.35 mL) and pyridine (0.52 mL), and the mixture was stirred at room temperature for 1.5 hours. To the reaction solution was added water, and the organic layer was washed with water and a saturated sodium hydrogen carbonate aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate) to give the title compound (0.15 g).

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol)
  5. dissolutionThis compound (0.22 g) was dissolved in dichloromethane (5.3 mL)
  6. additionTo the mixture were added ethyl oxalyl chloride (0.35 mL) and pyridine (0.52 mL)
  7. stirringthe mixture was stirred at room temperature for 1.5 hours
  8. additionTo the reaction solution was added water
  9. washthe organic layer was washed with water
  10. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-02bc2c3047b34c9bb0072c89c92aca11
Source dataset
uspto-grants-2012_09
Patent number
US08263622B2

Reaction notes

Loading…