Aluminium lithium hydride → (5-Chloro-1-methyl-1H-indol-2-ylmethyl)methylamine

To an ice-cold solution of 5-chloro-1-methyl-1H-indole-2-carboxylic acid methylamide (2.12 g, 9.5 mmol) in THF (15 mL) was added lithium aluminum hydride (19 mL of a 1 M solution in THF, 19.0 mmol). Once the addition was complete, the resulting slurry was heated to reflux overnight. The mixture was cooled in an ice bath and carefully quenched by the consecutive addition of water (0.90 mL), 15% aqueous NaOH (0.90 mL) and water (2.5 mL). The resulting mixture was filtered through diatomaceous earth and the filtrate concentrated to give the title (2.00 g, quantitative) compound as an orange oil: 1H NMR (300 MHz, CDCl3) δ 7.51 (d, J=1.8 Hz, 1H), 7.25-1.14 (m, 2H), 6.32 (s, 1H), 3.86 (s, 2H), 3.73 (d, J=4.8 Hz, 3H), 2.49 (s, 3H).

1. additionOnce the addition
2. temperaturethe resulting slurry was heated
3. temperatureto reflux overnight
4. temperatureThe mixture was cooled in an ice bath
5. customcarefully quenched by the consecutive addition of water (0.90 mL), 15% aqueous NaOH (0.90 mL) and water (2.5 mL)
6. filtrationThe resulting mixture was filtered through diatomaceous earth
7. concentrationthe filtrate concentrated
8. customto give the title (2.00 g, quantitative) compound as an orange oil

ORD record

ord-799ab6a6f9bb4b11bc5390779b74dc05

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07879872B2