Hydrochloric Acid → HCID 136337800, compound

HRID 1500104Notes

Reaction equation

HRID 1500104 reaction equation
N[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[C:5]([C:17]#[N:18])=[C:4]([O:19][CH3:20])[N:3]=1.N(OCCC(C)C)=O.[ClH:29]>C(#N)C.[Cu](Cl)Cl>[Cl:29][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[C:5]([C:17]#[N:18])=[C:4]([O:19][CH3:20])[N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 735342HCID 735342, compound

Product 1

HCID 136337800HCID 136337800, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

7.98 g (15.285 mmol) of 2-amino-4-(4-hydroxyphenyl)-6-methoxypyridine-3,5-dicarbonitrile are initially charged in 120 ml of acetonitrile, 6.175 ml (45.855 mmol) of isoamyl nitrite and 6.165 g (45.855 mmol) of copper(II) chloride are added and the mixture is stirred at room temperature overnight. 1N hydrochloric acid is added, and the reaction mixture is extracted with ethyl acetate. The organic phase is washed with saturated aqueous sodium bicarbonate solution and with water, dried over sodium sulphate and concentrated. The residue is purified on a silica gel column (mobile phase: toluene/ethyl acetate 2:1). This gives 1.3 g (23% 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 with water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated
  5. customThe residue is purified on a silica gel column (mobile phase: toluene/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-3f1c0edb5dae48bfa84ea1212b508429
Source dataset
uspto-grants-2015_12
Patent number
US09205077B2

Reaction notes

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