ChemicalBook CAS DataBase List 2,6-Dichloronicotinonitrile

2,6-Dichloronicotinonitrile synthesis

7synthesis methods

Product Name:2,6-Dichloronicotinonitrile
CAS Number:40381-90-6
Molecular formula:C6H2Cl2N2
Molecular Weight:173

76175-82-1

40381-90-6

General procedure for the synthesis of 2,6-dichloronicotinonitrile from N-(2,6-dichloropyridin-3-yl)acetamide: To a solution of dichloromethane (100 mL) containing 2,6-dichloro-3-acetamidopyridine (6.3 g, 55% purity) and pyridine (4.93 mL, 61 mmol) was slowly added trifluoroacetic anhydride (4.23 mL, 30 mmol). The reaction mixture was stirred overnight at room temperature and subsequently concentrated under reduced pressure. The crude product was purified by fast chromatography using 85% hexane and 15% ethyl acetate as eluents to give a light yellow product (1.77 g, 90% yield).HPLC analysis showed a retention time of 10.26 min (90% purity) and mass spectrometry analysis showed the molecular ion peak [M+H]+ = 172.9, and the theoretical molecular weight for the molecular formula C6H2Cl2N2 was 171.9 g/mol.

62068-78-4 Synthesis

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40381-90-6
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Yield:40381-90-6 89%

Reaction Conditions:

with tetraethylammonium chloride;trichlorophosphate at 80; for 24 h;

Steps:

General preparation of carbonitriles 8 and 14.
General procedure: The appropriate carboxamide 7 or 13 (189 mg, 0.99 mmol) was subjected to catalytic amounts of tetraethylammonium chloride (5% w/w) and POCl3 (5 ml) and heated under reflux at 80°C for 24 h. Excess POCl3 was removed in vacuo to leave a crude residue which was diluted with dichloromethane (10 ml) and filtered. The filtrate was washed successively with saturated aqueous K2CO3 (2 x 5 ml) and distilled water (5 ml). After drying over anhydrous Na2SO4, the solvent was evaporated to yield carbonitrile 8 or 14 which was sufficiently pure for use in the next reaction without purification. 2,6-Dichloronicotinonitrile (8)31 2,6-Dichloronicotinonitrile (8) was isolated as an off-white solid (152 mg, 89% yield). 1H NMR (300 MHz, CDCl3) δ 7.95 (d, J 8.1 Hz, 1H), 7.43 (d, J 8.1 Hz, 1H).

References:

Basson, Adriaan E.;Bode, Moira L.;Changunda, Charles R. K.;Rousseau, Amanda L. [Arkivoc,2021,vol. 2020,# 3,p. 152 - 170]

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40381-90-6
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References

91467-46-8 Synthesis