Hydrochloric Acid → HCID 117770470, compound

HRID 1526391Notes

Reaction equation

HRID 1526391 reaction equation
N[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[N:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([C:16]#[N:17])[C:9]1=[O:18].N([O-])=O.[Na+].C(=O)([O-])O.[Na+].[ClH:28]>[Cu]Cl>[Cl:28][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[N:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([C:16]#[N:17])[C:9]1=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 117770390HCID 117770390, compound

Product 1

HCID 117770470HCID 117770470, compound

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Procedure

To a mixture of 3′-amino-4-methoxy-2-oxo-2H-[1,4′-bipyridine]-3-carbonitrile obtained in Step B (1.00 g) and 1N hydrochloric acid (20 mL) was slowly added an aqueous solution (3 mL) of sodium nitrite (0.31 g) at 0° C., and the mixture was stirred for 2 hr. This reaction mixture was added to a mixture of copper(I) chloride (0.30 g) and 1N hydrochloric acid (5 mL) at 0° C., and the mixture was stirred at room temperature for 16 hr. The reaction mixture was slowly poured into saturated sodium hydrogen carbonate solution, and the mixture was extracted with a mixed solvent of tetrahydrofuran/ethyl acetate=1/1. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.40 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hr
  2. extractionthe mixture was extracted with a mixed solvent of tetrahydrofuran/ethyl acetate=1/1
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1ff2e02627f14a62aea40c7e76153fd4
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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