Electric Literature of 4421-09-4,Some common heterocyclic compound, 4421-09-4, name is 3,4-(Methylenedioxy)benzonitrile, molecular formula is C8H5NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
DIPEA (12.17 ml, 69.7 mmol) was added to a suspension of piperonylonitrile (5 g, 34.0 mmol) and hydroxylamine hydrochloride (4.72 g, 68.0 mmol) in EtOH (75 mL). After stirring at 20 C. for 21.5 h, the reaction mixture was concentrated to dryness. The resulting colorless oil was cooled to 0 C. and cold water was added (75.0 mL) and the mixture was stirred for 30 minutes to give a white slurry. The solids were filtered, washed with water (2×15 mL) and the resulting solid dried at 40 C. under high vacuum until constant weight to afford Intermediate 6a (Z)-N?-hydroxybenzo[d][1,3]dioxole-5-carboximidamide (5.76 g, 94% yield) as a white solid: 1H NMR (DMSO-d6) is consistent with the desired product; MS m/z 181.1 (MH+); HPLC 100%, Rt=0.16 (0.31) min. Alternatively DIPEA can be replaced by sodium carbonate or commercial sodium ethoxide while working in ethanol as solvent for the reaction. Except when commercially available, all N?-hydroxycarboximidamides cited in the examples hereafter were prepared following the recipe outline before for intermediate 6a with the appropriate nitrile precursor and including its variation on the nature of the base used.
The synthetic route of 4421-09-4 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Lamarre, Daniel; US2015/133495; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts