Chloride → 2-(5-Chloropyridin-3-yl)acetonitrile

HRID 512141

Reaction equation

[Cl-:1].S(Cl)(Cl)=O.[C-]#N.[K+].FC(F)(F)[C:11]1[N:16]=[CH:15][C:14]([CH2:17][C:18]#[N:19])=[CH:13][CH:12]=1>>[Cl:1][C:12]1[CH:13]=[C:14]([CH2:17][C:18]#[N:19])[CH:15]=[N:16][CH:11]=1

Participants

Reactant 4

HCID 312Chloride2×

HCID 9032Potassium Cyanide

HCID 24386Thionyl Chloride

HCID 508511273-Pyridineacetonitrile, 6-(trifluoromethyl)-

Product 1

HCID 552659022-(5-Chloropyridin-3-yl)acetonitrile

Procedure

Conversion of the hydroxyl group to the chloride using thionyl chloride, followed by the displacement of the chloride by potassium cyanide was performed using the same procedures described for (6-trifluoromethyl-pyridin-3-yl)-acetonitrile. 1H NMR (400 MHz, CDCl3) δ ppm 8.55 (d, J=2.0 Hz, 1 H), 8.50 (d, J=1.1 Hz, 1 H), 7.73 (s, 1 H), 4.58 (s, 2 H). MS m/z 153.0

Sources & evidence

ORD record: ord-7629e815c06247809eb898374acc3379
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102591B2

Linked notes

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