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o-Toluidine (55 g) was mixed with 100 ml dry pyridine and 200 ml dry tetrahydrofuran in a 1-L 3-necked round bottom flask fitted with a Trubore stirrer, thermometer and a dropping funnel, under nitrogen. Then, with cooling in a refrigerated bath, valeryl chloride (60.3 g) was added dropwise over 1 hour. The mixture was stirred for another hour at room temperature and then poured onto 500 g ice and water. The precipitate was washed repeatedly with water on a Buchner funnel. The precipitate (88.9 g, 93%) was cyclized according to Verley and Bedure, 1925, Bull. Soc. Chim. Fr. (37): 190 to afford 2-n-butyl indole (67.4 g, 84%) as a very slightly yellow oil.

1. customfitted with a Trubore stirrer
2. temperatureThen, with cooling in a refrigerated bath
3. washThe precipitate was washed repeatedly with water on a Buchner funnel