Hydrochloric Acid → HCID 22463777, compound

Participants

Reaction Steps

A solution of ethyl 4-acetoxy-6-morpholino-2-naphthoate (12.0 g, 34.9 mmol) and sodium hydroxide (8.4 g, 210 mmol) in water (200 cm3) and ethanol (40 cm3) was maintained at 80-90° C. for 3 hours. The cooled solution was poured into water (750 cm3) and cautiously neutralised with HCl (2M). The resulting suspension was extracted with EtOAc.(5×100 cm3). The combined extracts were dried (Na2SO4) and evaporated to give a brown solid. This solid was dissolved in methanol (200 cm3) containing c. H2SO4 (˜3 cm3) and was refluxed for 5 hours. The cooled mixture was diluted with water (900 cm3) and aq. sat. NaHCO3 solution (100 cm 3) then extracted with EtOAc (6×50 cm3). The combined extracts were washed with aq. sat. NaHCO3 (4×100 cm3) and water (100 cm3). Removal of the dried (Na2SO4) EtOAc gave a pale brown solid which was recrystallised from EtOAc/hexane to afford methyl 4-hydroxy-6-morpholino-2-naphthoate (yield=5.14 g, theoretical yield=10.0 g, 51.2%, m.p.=231-233.5° C. (uncorrected)).

Provenance & Evidence