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ChemicalBook CAS DataBase List 1-Naphthoyl chloride

1-Naphthoyl chloride synthesis

9synthesis methods
-

Yield:879-18-5 100%

Reaction Conditions:

with thionyl chloride in toluene; for 2 h;Reflux;

Steps:

General Procedure for Synthesis of Carboxamide Derivatives 1-8c

General procedure: Method A: Naphthalene-1-carboxylic acid (5.8 mmol) was dissolved in dry hot toluene (40 mL) and thionyl chloride (8.0 mmol) was added. After 2 h of refluxing, solvent and excessive thionyl chloride were evaporated under reduced pressure giving napthalene-1-carbonyl chloride as colourless liquid in quantitative yield. The product forms colourless needles after cooling. Mp. 18-19 °C (26 °C [54]). Naphthalene-1-carbonyl chloride (5.8 mmol), triethylamine (8.7 mmol) and corresponding substituted aniline (5.8 mmol) were dissolved in dry dichloromethane (30 mL) and the mixture was stirred for 12 h at ambient temperature. The solvent was evaporated under reduced pressure, the solid residue washed with 10% HCl, and the crude product was recrystallized from propan-2-ol with addition of active carbon.

References:

Gonec, Tomas;Kos, Jiri;Nevin, Eoghan;Govender, Rodney;Pesko, Matus;Tengler, Jan;Kushkevych, Ivan;Stastna, Vendula;Oravec, Michal;Kollar, Peter;O'mahony, Jim;Kralova, Katarina;Coffey, Aidan;Jampilek, Josef [Molecules,2014,vol. 19,# 7,p. 10386 - 10409]

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