2-Chloropyridine-4-carboxylic acid tert-butyl ester Chemical Properties

Boiling point:

287.4±20.0 °C(Predicted)

Density 

1.173±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

-1.27±0.10(Predicted)

Appearance

White to off-white Solid

CAS DataBase Reference

295349-62-1(CAS DataBase Reference)

Safety Information

HS Code 

2933399990

2-Chloropyridine-4-carboxylic acid tert-butyl ester Usage And Synthesis

Uses

2-Chloroisonicotinic acid tert-butyl ester is a useful research chemical for organic synthesis and other chemical processes.

Synthesis

General procedure for the synthesis of tert-butyl 2-chloroisonicotinate from 2-chloroisonicotinic acid and N,N-dimethylformamide di-tert-butyl acetal: 10.0 g (63.4 mmol) of 2-chloroisonicotinic acid was dissolved in 100 ml of chloroform and heated to reflux temperature. A total of 91.2 ml (380 mmol, 6 eq.) of N,N-dimethylformamide di-tert-butyl acetal was added in three additions of 30.4 ml each at the beginning of the reaction, after 1 h and after 2 h. Upon completion of the reaction, it was cooled down to room temperature, and the reaction mixture was diluted with ethyl acetate, washed with water, sodium bicarbonate solution, and saturated saline in that order, and dried over anhydrous sodium sulfate. The residue was purified by silica gel column chromatography (fast column chromatography, eluent gradient from hexane to hexane/ethyl acetate 95/5) to give 7.6 g (35.6 mmol, 56% yield) of white solid product. Mass spectrum (LC/MS): m/z 158 = [M + H - tBu]+. 1H-NMR (300 MHz, CDCl3): δ 8.55 (d, 1H), 7.85 (s, 1H), 7.76 (d, 1H), 1.64 (s, 9H).

References

[1] Patent: US2008/132477, 2008, A1. Location in patent: Page/Page column 28
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 1, p. 110 - 130
[3] Patent: WO2014/141171, 2014, A1. Location in patent: Page/Page column 17; 18

2-Chloropyridine-4-carboxylic acid tert-butyl ester(295349-62-1)Related Product Information

• 2-Chloronicotinic acid
• tert-Butyl bromoacetate
• Methyl acrylate
• 2-Chloro-4-pyridinecarboxylic acid
• TERT-BUTYL PROPIONATE
• tert-Butyl acrylate
• 2-Butoxyethanol
• Buprofezin
• tert-Butyl methacrylate
• tert-Butyl acetoacetate
• Butyl acetate
• Isobutyl chloroformate
• tert-Butanol
• Tris(trimethylsilyl)phosphate
• Butyl acrylate
• tert-butyl 2-bromo-6,7-dihydropyrazolo[1,5-a]pyrazine-5(4H)-carboxylate
• (2-BROMO-PYRIDIN-4-YL)CARBAMIC ACID TERT-BUTYL ESTER
• Tert-Butyl 2-Iodo-6,7-Dihydropyrazolo[1,5-A]Pyrazine-5(4H)-Carboxylate(WX141846)