Reaction #710583

Reaction equation

Sodium triacetoxyborohydride

8-hydroxy-quinoline-2-carboxaldehyde

histamine

→

2-{[2-(1H-imidazol-4-yl)-ethylamino]-methyl}-quinolin-8-ol

Yield 61.5%

Solvents

dichloroethane

Conditions

Workup

1. 1
   workup.WAITThe mixture was left
2. 2
   Concentrationneutralized (aqueous NaHCO3), and concentrated

Procedure

Sodium triacetoxyborohydride (225 mg, 1.061 mmol) was added to a stirred solution of 8-hydroxy-quinoline-2-carboxaldehyde 4 (200 mg, 1.156 mmol) and histamine (128 mg, 1.152 mmol) in dichloroethane (10 mL). The mixture was left to stir at RT for 16 h, neutralized (aqueous NaHCO3), and concentrated. The resulting residue, after column chromatography on silica (ethyl acetate/i-PrOH/2 N NH4OH, 6:2:1), afforded 2-{[2-(1H-imidazol-4-yl)-ethylamino]-methyl}-quinolin-8-ol F1 as a straw-colored solid (190 mg, 61%). The above method was repeated using other amines: 2-(aminomethyl)pyridine gave F2 and 2-(2-methylaminoethyl)pyridine gave F3, data given in Table 2.

Source