Acetic Acid → HCID 23295350, compound

Participants

Reaction Steps

In a 500-ml flask, place 46.05 g (0.2 m) of the blocked aminobenzaldehyde, 125 ml of acetic acid and 23.23 g (0.4 m) of acetone. Heat the mixture to 30 C. Add 11.78 g (0.2 m) of borane-dimethylamine complex slowly keeping the temperature below 50 C. Stir the mixture at 50 C. for 1 hour, and cool to room temperature. Add 200 ml of water and stir for 15 minutes. Collect solids, wash with water, and deliquor as much as possible. In a 500-ml flask, place the wet intermediate, 100 ml of methanol, and 60 g of 50% NaOH solution. Heat the mixture under reflux for 1 hour. Add 120 ml of hot water and distill off methanol till approximately 120 ml of distillate is collected and pot temperature reaches close to 100 C. Heat the mixture under reflux for 1 hour, and then cool to room temperature. Add 150 ml of propyl acetate, stir for 5 minutes, and let layers settle. Separate bottom water layer. Wash the propyl acetate solution with 100 ml of brine. Dry over magnesium sulfate and distill propyl acetate under a reduced pressure to a red viscous oil. Add 150 ml of heptanes with vigorous stirring. Stir the resulting slurry at room temperature for 45 minutes. Collect product, wash with heptanes, and dry to give 28.35 g (80%) of 4-isopropylamino-2-methylbenzaldehyde as yellow solids.

Provenance & Evidence