Aluminium lithium hydride → HCID 68555288, Verbindung
Reaktionsgleichung
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([N:11]=O)[CH2:6][C:5]2([CH3:14])[CH3:13].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([NH2:11])[CH2:6][C:5]2([CH3:14])[CH3:13]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 5-fluoro-3,3-dimethyl-1-nitroso-2,3-dihydro-1H-indole (4.03 g, 20.75 mmol) in THF (70 mL) at 0° C. is added a solution of LiAlH4 (40 mL, 40 mmol) in THF dropwise. The mixture is allowed to warm to rt and stirred overnight. The mixture is quenched with a saturated aqueous solution of Rochelle's Salt. The resulting mixture is stirred until a slurry is obtained. The organic phase is separated, washed with 10% aqueous HCl, saturated aqueous NaHCO3, water and brine, dried (MgSO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 25% EtOAc in heptane to afford 5-fluoro-3,3-dimethyl-2,3-dihydro-indol-1-ylamine (3.51 g, 94%) as an oil. MS: 181 (M+H). 1H NMR (300 MHz, CD3Cl)): δ 6.85-6.78 (m, 1H), 6.75-6.68 (m, 2H), 3.44 (br s, 2H), 3.14 (s, 2H), 1.28 (s, 6H).