Hydrochloric Acid → HCID 58297349, compound

HRID 1500102Notes

Reaction equation

HRID 1500102 reaction equation
N[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:12][CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([O:22][CH2:23][CH3:24])[N:3]=1.N(OCCC(C)C)=O.[ClH:33]>C(#N)C.[Cu](Cl)Cl>[Cl:33][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:12][CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([O:22][CH2:23][CH3:24])[N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 67025545HCID 67025545, compound

Product 1

HCID 58297349HCID 58297349, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

14.8 g (45.631 mmol) of 2-amino-6-ethoxy-4-[4-(2-hydroxyethoxy)phenyl]pyridine-3,5-dicarbonitrile are initially charged in 830 ml of acetonitrile, 32.07 g (273.785 mmol) of isoamyl nitrite and 36.81 g (273.785 mmol) of copper(II) chloride are added and the mixture is stirred at 60° C. for 3 hours. 800 ml of 1N hydrochloric acid are added, and the reaction mixture is extracted with ethyl acetate. The organic phase is washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated. The residue is triturated with ethanol, and the solid is filtered off, washed with ethanol and dried under high vacuum. As the mother liquor still contains product, it is adsorbed onto 35 g of silica gel and purified on a silica gel column (mobile phase: cyclohexane/ethyl acetate 2:1→1:1). This gives a total of 11.9 g (72% of theory) of the target compound.

Workup

  1. extractionthe reaction mixture is extracted with ethyl acetate
  2. washThe organic phase is washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated
  5. customThe residue is triturated with ethanol
  6. filtrationthe solid is filtered off
  7. washwashed with ethanol
  8. customdried under high vacuum
  9. custompurified on a silica gel column (mobile phase: cyclohexane/ethyl acetate 2:1→1:1)
  10. customThis gives a total of 11.9 g (72% of theory) of the target compound

Sources & evidence

ORD record
ord-156e69af77474c4e94cbe0eb15d5049d
Source dataset
uspto-grants-2015_12
Patent number
US09205077B2

Reaction notes

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