Aluminium lithium hydride → HCID 67969245, compound
Reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH:12]=[CH:13][N+:14]([O-])=O)[N:8]2[CH3:11])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH2:12][CH2:13][NH2:14])[N:8]2[CH3:11])=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 6-bromo-1-methyl-2-(2-nitrovinyl)-1H-indole (871 mg, 3.10 mmol) in THF (60.0 mL) at 0° C. was added LiAlH4 (2.0 M in THF, 6.20 mL, 12.4 mmol) dropwise. The reaction mixture was allowed to warm to room temperature over 5 h and then quenched with water and 10% aqueous NaOH (20 mL) at 0° C. to form a precipitate which was filtered through filter paper. The filtrate was extracted with EtOAc. The extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by flash chromatography (silica gel, CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 90:10 to 20:80) gave the title compound (329 mg, 42%) as a brown oil: 1H NMR (500 MHz, CDCl3) δ 7.42 (s, 1H), 7.38 (d, J=8.5 Hz, 1H), 7.17 (dd, J=8.5, 2.0 Hz, 1H), 6.27 (d, J=1.0 Hz, 1H), 3.65 (s, 3H), 3.08-3.55 (m, 2H), 2.92-2.87 (m, 2H).