Sodium Hydroxide → 1-Chloro-3-ethoxyisoquinoline

Participants

Reaction Conditions

Reaction Steps

3-Ethoxyisoquinoline N-oxide (1.15 g, 6.1 mmol) was taken up in POCl3 (5 mL) at rt and then heated to 120° C. under an atmosphere of Ar for 2 h. Following cooling to rt, the reaction was diluted with CHCl3 and poured into icewater (20 mL) and the resulting solution was placed in an ice bath and treated with 10M NaOH until pH 10 with vigorous stirring. Following extraction with CHCl3, the combined organics were washed with brine and dried over anhydrous MgSO4. Following concentration in vacuo, purification on SiO2 (3-15% EtOAc/hex) afforded 0.51 g (40%) of 1-chloro-3-ethoxyisoquinoline. LCMS found 208.1 [M+H]+.

Provenance & Evidence