Hydrochloric Acid → HCID 63897176, compound

Participants

Reaction Conditions

Reaction Steps

Add thionyl chloride (67.6 mL, 928 mmol) dropwise to a solution of 2,3-dimethoxybenzoic acid (132 g, 714 mmol) and DMF (1.32 mL) in toluene (528 mL) maintained at 40° C. Stir the solution for 1 h at 40° C. after the addition is complete. Concentrate the mixture in vacuo and dissolve the residue in dichloromethane (528 mL). Warm the mixture to reflux and add tert-butyl alcohol (203.4 mL). Add pyridine (86.6 mL) dropwise over 5 min followed by addition of N,N-dimethylpyridin-4-amine (4.36 g, 35.7 mmol) and stir the mixture 1 h while cooling to ambient temperature. Dilute the mixture with water (200 mL) and acidify the mixture (pH=2) with 2 N hydrochloric acid. Separate the phases and wash the organic phase with 0.5 N hydrochloric acid (2×30 mL). Wash the organic phase with 15% potassium carbonate, water, and brine. Concentrate the organic phase in vacuo to yield the title compound (141.2 g, 83%) as a white solid. ES/MS m/z 165 [M-(C4H9O)]+.

Provenance & Evidence