Ammonia → HCID 12740033, compound

Participants

Reaction Steps

Small pieces of ferric nitrate nonahydrate were added to 75 ml of liquid ammonia, and subsequently 0.733 g of metallic sodium was added little by little. The mixture was stirred for 30 minutes. To the stirred mixture was added dropwise over the course of 10 minutes a solution of 6.25 g of methyl 11-methoxy-5H-dibenzo[a,d]cyclohepten-2-acetate obtained in Example 12 in 12 ml of dry toluene. The mixture was stirred for 25 minutes, and a solution of 1.98 ml of methyl iodide in 2 ml of dry toluene was added dropwise over the course of 2 minutes. The mixture was further stirred for 1 hour, and then 1.83 g of ammonium chloride and 12 ml of toluene were added. Ammonia was released at room temperature. Then, 24 ml of 10% hydrochloric acid was added under ice cooling and stirring, and the mixture was stirred for 15 minutes. Ether (100 ml) and 100 ml of water were added to extract the solution. The organic layer was successively washed with water, a 10% aqueous solution of sodium thiosulfate and a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was distilled off. The residue was chromatographed on a silica gel column using benzene as an eluent. From the eluate, 5.91 g of methyl 2-(11-methoxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionate was obtained as a colorless oily substance.

Provenance & Evidence