Acetic Acid → 3-Methyl-N-propylidene-1H-indol-1-amine

Participants

Reaction Conditions

Reaction Steps

A solution of 10 kg (76.2 mol) 3-methylindole in 50 kg NMP is prepared, and add an initial amount of 0.08–0.12 eq. KOtBu-solution to the 3-methylindole solution. The HOSA and the KOtBu solutions are added over a period of 120 min simultaneously and proportionally over mass flow meters at 20° C. to the reaction mixture. After the addition is completed, add to the resulting dark brown suspension 6.9 L (381 mol) water, 13.7 kg (228.6 mol) acetic acid (100%) and 7.5 kg (129.2 mol) propionaldehyde. Stir the mixture at 20° C. for ˜1 h, until completion of the reaction. The reaction mixture is then worked-up by adding 248 L water and 42 kg n-heptane. Unwanted salts precipitate from the reaction mixture. The resulting suspension is filtered and the phases are separated. The water phase is again extracted 3-times with 42 kg n-heptane. The combined organic phases are washed two times with 63 L water. The resulting brown heptane-solution is evaporated to dryness. This results in 11.6–12.5 kg 3-methyl-N-(propylidene)-1H-indol-1-amine (yield 81–90%) as a brown liquid.

Provenance & Evidence