Hydrochloric Acid → 3-(Amino-benzoyl)thiophene

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Reaction Conditions

Reaction Steps

The 3-(2-thenoyl)aniline may be prepared as follows: Stannous chloride in the dihydrate form (22.8 g) is added, at a temperature in the vicinity of 4° C., to a suspension of 3-(2-thenoyl)nitrobenzene (6.8 g) in a 3.7N solution (130 cc) of hydrogen chloride in ethanol, in the course of 40 minutes. After stirring at a temperature in the vicinity of 4° C. for 1 hour and then at a temperature in the vicinity of 20° C. for 1 hour, the solution obtained is heated at a temperature in the vicinity of 78° C. for 1 hour. The solvent is evaporated off under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 50° C. The residue obtained is taken up with a mixture of distilled water (50 cc) and diethyl ether (100 cc), to which an aqueous 10N sodium hydroxide solution (130 cc) is added at a temperature in the vicinity of 15° C. The organic phase is separated and the aqueous phase is extracted 4 times with diethyl ether (400 cc in total). The ether extracts are combined, washed 3 times with distilled water (300 cc in total), dried over anhydrous magnesium sulphate, treated with decolourizing charcoal (0.5 g), and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 40° C. 2-(3-Thenoyl)aniline (5.7 g) in the form of yellow crystals m.p. 105° C., is thereby obtained.

Provenance & Evidence