ChemicalBook CAS DataBase List 4-CHLORO-PYRIDINE-2-CARBONITRILE

4-CHLORO-PYRIDINE-2-CARBONITRILE synthesis

13synthesis methods

Product Name:4-CHLORO-PYRIDINE-2-CARBONITRILE
CAS Number:19235-89-3
Molecular formula:C6H3ClN2
Molecular Weight:138.55

99586-65-9 Synthesis

99586-65-9
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$14.00/5g

19235-89-3
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$10.00/1g

Yield:19235-89-3 90%

Reaction Conditions:

with triethylamine;trifluoroacetic anhydride in ethyl acetate at -5 - 20; for 1.25 h;

Steps:

5.1.2. 4-Chloropicolinonitrile (3)
The compound 2 (7.0 g, 44.7 mmol) and triethylamine (13 ml, 93.7mmol) were dissolved in dry EtOAc (50 ml) and the stirred solution was cooled to -5 °C in an ice-salt bath. Trifluoroacetic anhydride (13 ml, 92.2 mmol) was added dropwise to the chilled mixture over 45 min. The ice-salt bath was then removed and the reaction was warmed to room temperature and then stirred for another 30 min. The completion of reaction was detected by TLC, 10% aqueous K₂CO₃ (100 ml) was added, and the reaction mixture was allowed to stir for further 20 min. The mixture was extracted with EtOAc (3 × 50 ml), the combined organic layers were washed with brine (2 × 50 ml), dried over anhydrous Na₂SO₄, and concentrated under reduced pressure to give compound 3 (5.6 g, 90% yield) as a white solid, mp 84-85 °C; ¹H NMR (DMSO-d₆, 400 MHz): δ 7.54-7.56 (dd, J = 5.0 and 2.0 Hz, 1H), 7.74 (m, 1H), 8.65 (d, J = 5.0 Hz, 1H); ESI-MS m/z: 139[M+H]⁺; Anal. Calcd for C₆H₃ClN₂ (%): C 52.01, H 2.18, N 20.22; Found: C 51.94, H 2.14, N 20.28.

References:

Zhan, Wenhu;Li, Yanyang;Huang, Weiping;Zhao, Yanjin;Yao, Zhenglin;Yu, Shanyou;Yuan, Shoujun;Jiang, Falong;Yao, Shan;Li, Shuxin [Bioorganic and Medicinal Chemistry,2012,vol. 20,# 14,p. 4323 - 4329] Location in patent:experimental part

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