反应详情

温度

15 °C

Prepare a solution of 6.4 kg (54.6 mol) indole in 25 kg NMP. Add to this solution the HOSA and the KOtBu solutions as prepared above over a period of 180 min simultaneously and proportionally over mass flow meters and maintain the reaction mixture at 15° C. After the addition is completed, add to the resulting dark brown suspension 4.3 L (239 mol) water, 9.7 kg (161.5 mol) acetic acid (100%) and 5.3 kg (91.3 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 180 L water and 21 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 4-times with 21 kg n-heptane. The combined organic phases are washed two times with 45 L water. The resulting brown heptane-solution is evaporated to a 15–25% solution. This results in 6.3–7.0 kg N-(propylidene)-1H-indol-1-amine (yield 67–74%, corrected for 19.7–24.1% assay) as a brown liquid.

1. additionAdd to this solution the HOSA
2. additionAfter the addition
3. customuntil completion of the reaction
4. customUnwanted salts precipitate from the reaction mixture
5. filtrationThe resulting suspension is filtered
6. customthe phases are separated
7. washThe combined organic phases are washed two times with 45 L water
8. customThe resulting brown heptane-solution is evaporated to a 15–25% solution