Triethylamine → 6-Nitro-1H-indole-3-carbonitrile

Temperature

0 °C

6.1 g 6-nitro-1H-indole are dissolved in 100 ml acetonitrile and cooled to 0° C. A solution of 3.2 ml chlorosulphonyl isocyanate in 25 ml acetonitrile is added dropwise and the mixture is stirred for 2 hours. Then a solution of 5 ml triethylamine in 25 ml acetonitrile is added dropwise. The mixture is stirred for 1 hour at ambient temperature and for 50 minutes at 80° C. Then the solvents are eliminated in vacuo, the residue is extracted from cold water, the solid is suction filtered and washed successively with water, saturated sodium hydrogen carbonate solution and water. The solid thus obtained is dried in the desiccator. Then the solid is taken up in 500 ml dichloromethane/methanol 95:5 and stirred with some aluminium oxide. It is suction filtered through a thin layer of aluminium oxide and washed with 400 ml dichloromethane/methanol 95:5. The filtrate is evaporated down in vacuo and the residue is dried in vacuo.

1. stirringThe mixture is stirred for 1 hour at ambient temperature and for 50 minutes at 80° C
2. extractionthe residue is extracted from cold water
3. filtrationfiltered
4. washwashed successively with water, saturated sodium hydrogen carbonate solution and water
5. customThe solid thus obtained
6. customis dried in the desiccator
7. stirringstirred with some aluminium oxide
8. filtrationfiltered through a thin layer of aluminium oxide
9. washwashed with 400 ml dichloromethane/methanol 95:5
10. customThe filtrate is evaporated down in vacuo
11. customthe residue is dried in vacuo

ORD record

ord-96b18bc37cec4f40a73214e772404707

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08232312B2