4-Aminophenol → HCID 59398526, compound

Participants

Reaction Steps

P-Aminophenol (8.4 g, 77 mmol) and potassium t-butoxide (14.4 g, 77 mmol) were dissolved in NMP (150 mL), and potassium carbonate (9 g, 39 mmol) was added thereto. The resulting mixture was stirred at room temperature for 1 hour, and an NMP (10 mL) solution of 1-benzyloxymethyl-4-chloro-1H-pyrrolo[2,3-b]pyridine (20 g, 73.3 mmol) was dropwise added thereto at 180° C. over 15 minutes. Subsequently, the mixture was stirred for 2 hours. The reaction container was cooled, and the content was poured on ice (650 g) and extracted with ethyl acetate (500 mL) three times. The combined organic layer was washed with saturated brine (150 mL) twice, dried, and concentrated. The residue was purified by silica-gel column chromatography (manufactured by Fuji Silysia, BW300, 7.5 cm×25 cm, n-hexane:EtOAc=1:1) to give 4-(1-benzyloxymethyl-1H-pyrrolo[2,3-b]pyridin-4-yloxy)aniline (21.9 g) as a light-yellow syrup (yield: 86%).

Provenance & Evidence