Hydrochloric Acid → HCID 86654213, compound

HRID 1500100Notes

Reaction equation

HRID 1500100 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][CH3:23])[N:3]=1.N(OCCC(C)C)=O.[ClH:32]>C(#N)C.[Cu](Cl)Cl>[Cl:32][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][CH3:23])[N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 67025736HCID 67025736, compound

Product 1

HCID 86654213HCID 86654213, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

3.3 g (10.634 mmol) of 2-amino-4-[4-(2-hydroxyethoxy)phenyl]-6-methoxypyridine-3,5-dicarbonitrile are initially charged in 300 ml of acetonitrile, 8.578 g (63.806 mmol) of copper(II) chloride and 8.59 ml (63.806 mmol) of isoamyl nitrite 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 water, dried over sodium sulphate and concentrated. The reaction mixture is purified by preparative HPLC (acetonitrile/water: 10:90→95:5). This gives 2.11 g (58% 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 water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated
  5. customThe reaction mixture is purified by preparative HPLC (acetonitrile/water: 10:90→95:5)

Sources & evidence

ORD record
ord-22f54a99a38f40fb86e0e546ac31929c
Source dataset
uspto-grants-2015_12
Patent number
US09205077B2

Reaction notes

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