4-Cyanoindole → (1H-indol-4-yl)methanamine

To a solution of 4-cyanoindole (7.5 g, 53 mmol) in THF (100 ml) was added at rt a 1.0M solution of lithium aluminum hydride in THF (100 ml, 100 mmol). The mixture was refluxed for 30 min then cooled to rt. The reaction mixture was quenched with 1N NaOH and filtered. The filtrate was acidified with 1N HCl and stirred at rt for 10 min. The pH was adjusted to ˜8 by adding sat NaHCO3 and extracted with n-butanol. The layers were separated and the organic layer was concentrated to dryness. The residue was triturated with methanol. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure to afford the desired product as a solid that was further dried under high vacuum at 50° C. (7.27 g, 94% yield).

1. temperatureThe mixture was refluxed for 30 min
2. customThe reaction mixture was quenched with 1N NaOH
3. filtrationfiltered
4. additionby adding
5. extractionextracted with n-butanol
6. customThe layers were separated
7. concentrationthe organic layer was concentrated to dryness
8. customThe residue was triturated with methanol
9. customInsoluble materials were removed by filtration
10. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-407d9752b0d84079b3b403528db7c4c5

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08404859B2