Fe(ClO4)3·H2O-Catalyzed Ritter Reaction: A Convenient Synthesis of Amides from Esters and Nitriles

Chengliang Feng; Bin Yan; Guibo Yin; Junqing Chen; Min Ji

doi:10.1055/s-0037-1610658

Synlett, Table of Contents

Synlett 2018; 29(17): 2257-2264
DOI: 10.1055/s-0037-1610658

letter

Fe(ClO₄)₃·H₂O-Catalyzed Ritter Reaction: A Convenient Synthesis of Amides from Esters and Nitriles

Chengliang Feng

^aInstitute of Pharmaceutical Engineering, Jiangsu College of Engineering and Technology, Nantong, Jiangsu 226000, P. R. of China Email: fcl085620@163.com

,

Bin Yan

^aInstitute of Pharmaceutical Engineering, Jiangsu College of Engineering and Technology, Nantong, Jiangsu 226000, P. R. of China Email: fcl085620@163.com

,

Guibo Yin

^aInstitute of Pharmaceutical Engineering, Jiangsu College of Engineering and Technology, Nantong, Jiangsu 226000, P. R. of China Email: fcl085620@163.com

,

Junqing Chen

^bSchool of Biological Sciences & Medical Engineering, Southeast University, Nanjing, Jiangsu 211189, P. R. of China

,

Min Ji*

^bSchool of Biological Sciences & Medical Engineering, Southeast University, Nanjing, Jiangsu 211189, P. R. of China

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Abstract

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Abstract

An efficient and inexpensive synthesis of N-substituted amides from the Ritter reaction of nitriles with esters catalyzed by Fe(ClO₄)₃·H₂O is described. Fe(ClO₄)₃·H₂O is an economically efficient catalyst for the Ritter reaction under solvent-free conditions. Reactions of a range of esters (benzyl, sec-alkyl, and tert-butyl esters) with nitriles (primary, secondary, tertiary, and aryl nitriles) were performed to provide the corresponding amides in high to excellent yields.

Key words

Ritter reaction - Fe(ClO₄)₃·H₂O - esters - nitriles - solvent-free reactions

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References

References and Notes
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30 Typical Experimental Procedure for the Reaction of Benzonitrile and Esters (Benzyl, sec-Alkyl and Primary Alkyl Esters) A mixture of benzonitrile (5 mmol), benzyl acetate (6 mmol), and Fe(ClO₄)₃·H₂O (5 mol%) was placed in a round-bottomed flask. Then, the reaction mixture was heated at 80 °C for 5 h. After completion of the reaction monitored by thin layer chromatography (TLC), water (10 mL) was added, and the reaction mixture was extracted with ethyl acetate (3 × 20 mL). The organic layers were collected, combined, washed with water (3 × 20 mL), dried with anhydrous Na₂SO₄, and concentrated under vacuum. The pure product was obtained by directly passing through a silica gel (200–300 mesh) column to give a white powder a (0.91 g, 87% yield). Compound a ¹H NMR (CDCl₃, 400 MHz): δ = 7.80 (m, 2 H), 7.78–7.25 (m, 8 H), 6.51 (s, 1 H), 4.64 (d, J = 5.8 Hz, 2 H) ppm. ¹³C NMR (CDCl₃, 100 MHz): δ = 167.4, 138.2, 134.4, 131.6, 128.8, 128.6, 127.9, 127.6, 127.0, 44.1 ppm.
31 Typical Experimental Procedure for the Reaction of Various Nitriles and Acetic Esters A mixture of 3-methylbenzonitrile (5 mmol), benzyl acetate (6 mmol), and Fe(ClO₄)₃·H₂O (5 mol%) was placed in a round-bottomed flask. Then, the reaction mixture was heated at 80 °C for 5 h. After completion of the reaction monitored by thin layer chromatography (TLC), water (10 mL) was added, and the reaction mixture was extracted with ethyl acetate (3 × 20 mL). The organic layers were collected, combined, washed with water (3 × 20 mL), dried with anhydrous Na₂SO₄, and concentrated under vacuum. The pure product was obtained by directly passing through a silica gel (200–300 mesh) column to give a white powder n (0.96 g, 86% yield). Compound n ¹H NMR (CDCl₃, 400 MHz): δ = 7.61–7.55 (m, 2 H), 7.34–7.28 (m, 7 H), 6.55 (s, 1 H), 4.62 (d, J = 5.64 Hz, 2 H), 2.37 (s, 3 H) ppm. ¹³C NMR (CDCl₃, 100 MHz): δ = 167.6, 138.4, 138.3, 134.3, 132.3, 128.8, 128.4, 127.9, 127.7, 127.6, 123.9, 44.1, 21.3 ppm.
32 Typical Experimental Procedure for the Reaction of Nitriles and di-tert-Butyl Malonate A mixture of 2-(3, 4-dichlorophenyl)acetonitrile (5 mmol), di-tert-butyl malonate (3 mmol), and Fe(ClO₄)₃·H₂O (5 mol%) was placed in a round-bottomed flask. Then, the reaction mixture was heated at 80 °C for 5 h. After completion of the reaction monitored by thin layer chromatography (TLC), water (10 mL) was added and the reaction mixture was extracted with ethyl acetate (3 × 20 mL). The organic layers were collected, combined, washed with water (3 × 20 ml), dried over anhydrous Na₂SO₄, and concentrated under vacuum. The pure product was obtained by directly passing through a silica gel (200–300 mesh) column to give a white powder 1m (1.08 g, 84% yield). Compound 1m ¹H NMR (400 MHz, CDCl₃): δ = 7.41–7.35 (m, 2 H), 7.12–7.10 (m, 1 H), 5.31 (s, 1 H), 3.40 (s, 2 H), 1.32 (s, 9 H) ppm. ¹³C NMR (100 MHz, CDCl₃): δ = 168.9, 135.6, 132.7, 131.2, 131.2, 130.6, 128.6, 51.6, 43.5, 28.7 ppm. HRMS: m/z calcd for C₁₂H₁₅Cl₂NO [M + H]⁺: 259.0531; found: 259.0533.

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