Hydrochloric Acid → HCID 67974255, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-iodo-7-methoxynaphthalen-2-amine (see Intermediate 6, product of step 3) (1.0 g, 3.34 mmol) in water (20 mL) and conc. HCl (20 mL) was added a solution of NaNO2 (230 mg, 3.34 mmol) in water (10 mL) dropwise at 0° C. and the reaction was stirred at 0° C. for 1 hour. Then CuCl (400 mg, 4.04 mmol) was added and the mixture was stirred at 20° C. for 2 hours. An aqueous/EtOAc workup was followed by purification by silica gel column (PE/EtOAc=100/1) to give 3-chloro-2-iodo-6-methoxynaphthalene (900 mg, yield 85%) as off-white solid. 1H NMR (CDCl3 300 MHz TMS): δ 8.29 (s, 1H), 7.84 (s, 1H), 7.60 (d, J=9.0 Hz, 1H), 7.13 (dd, J=9.0, 2.7 Hz, 1H), 6.99 (d, J=2.4 Hz, 1H), 3.91 (s, 3H).

Provenance & Evidence