Sulfuric Acid → HCID 178424567, compound

Participants

Reaction Steps

Sulfuric acid (18 M; 3.8 mL, 68 mmol) was added to N-(2,5-dimethylbenzyl)-2,2-dimethoxyacetamide (1.17 g, 4.92 mmol) at rt, and the solution was stirred at rt overnight. The solution was poured into ice, basified with NaOH (10 N) until pH>13, extracted with Et2O (3×30 ml), and the extracts were back-extracted with water (20 ml). The aqueous layer was neutralized with HCl until pH=7-8 and extracted with EtOAc (3×30 ml). The EtOAc extracts were washed with water (2×20 ml), brine (20 ml), dried over MgSO4, filtered, and concentrated in vacuo to give a brown solid. It was purified by prep. TLC eluting with 4% MeOH in DCM to give the title compound as yellow solid. 1H NMR (400 MHz, CDCl3): δ=2.46 (s, 3H), 2.55 (s, 3H), 6.84 (d, J=7.6 Hz, 1H), 6.98 (s, 1H), 7.16 (d, J=7.2 Hz, 1H), 8.61 (s, 1H). MS(ES+): m/z=173.43 (100) [MH+]. HPLC: tR=2.35 min (polar—5 min, ZQ3).

Provenance & Evidence