Nitric Acid → 7-Nitro-1,2,3,4-tetrahydroquinoline

Participants

Reaction Steps

Concentrated sulfuric acid (30.00 mL) was cooled to −10° C. with an ice/salt bath. To this, 1,2,3,4-tetrahydro-quinoline (10.60 g, 75.60 mmol) and a solution of nitric acid (99.5%, 4.80 g, 75.60 mmol) in sulfuric acid (15.00 mL) were added simultaneously within 1 hour, so that the temperature of the reaction mixture does not exceed 10° C. The mixture was stirred then for 2.5 hours at −5° C., then poured over ice and treated with sodium carbonate (0.10 kg) until pH 8-9 was reached. The solid was filtered, washing with water, then dissolved in dichloromethane. The organic phase was washed with water, dried over magnesium sulphate and evaporated. 7-Nitro-1,2,3,4-tetrahydro-quinoline was obtained as a viscous brown oil, 13.70 g (85%), 84% purity.

Provenance & Evidence