Hydrochloric Acid → 2-Chloro-6-methyl-4-(tetrahydro-2H-pyran-2-yl)pyridine-3,5-dicarbonitrile

HRID 1873581Notes

Reaction equation

N[C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)[C:5]([C:16]#[N:17])=[C:4]([CH3:18])[N:3]=1.N(OCCC(C)C)=O.[ClH:27]>C(#N)C.[Cu](Cl)Cl>[Cl:27][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)[C:5]([C:16]#[N:17])=[C:4]([CH3:18])[N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

610 mg (2.52 mmol) of the compound from Example 39A are initially charged in 44 ml of acetonitrile, and 590 mg (5.04 mmol) of isopentyl nitrite and 677 mg (5.04 mmol) of copper(II) chloride are added. The reaction mixture is stirred at 60° C. for 30 min. 40 ml of 1 N hydrochloric acid are then added to the mixture and the mixture is extracted three times with in each case 100 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate and the solvent is removed on a rotary evaporator. The product is used in the next reaction without further purification.

Workup

extractionthe mixture is extracted three times with in each case 100 ml of ethyl acetate
dry with materialThe combined organic phases are dried over magnesium sulfate
customthe solvent is removed on a rotary evaporator
customThe product is used in the next reaction without further purification

Sources & evidence

ORD record: ord-6095a4f546834cb89aeaf15bbe4bea82
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304412B2

Reaction notes

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