Hydrochloric Acid → 5-Methylbenzofuran-7-amine

Reaction equation

C(=[N:14][C:15]1[C:23]2[O:22][CH:21]=[CH:20][C:19]=2[CH:18]=[C:17]([CH3:24])[CH:16]=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl.[OH-].[Na+]>C1COCC1>[CH3:24][C:17]1[CH:16]=[C:15]([NH2:14])[C:23]2[O:22][CH:21]=[CH:20][C:19]=2[CH:18]=1

Participants

Procedure

Benzhydrylidene(5-methylbenzofuran-7-yl)amine (17.9 g, 0.57 mmol) was dissolved in THF (150 ml). 5N Hydrochloric acid (50 ml) was added thereto, followed by stirring at room temperature for 2 hours. A 5N aqueous sodium hydroxide solution (40 ml) was added to the reaction mixture, followed by extraction using ethyl acetate. The extract was sequentially washed with an aqueous saturated sodium hydrogen solution and an aqueous saturated sodium chloride solution. The organic layer was dried over magnesium sulfate and concentrated to dryness under reduced pressure. The residue was purified using silica gel column chromatography (n-hexane:ethyl acetate=50:1→10:1). The purified product was concentrated to dryness under reduced pressure, giving a dark brown oily substance of 5-methylbenzofuran-7-ylamine (2.5 g, yield: 30%).