Nitromethane → HCID 70622813, compound

Participants

Reaction Conditions

Reaction Steps

To a 100 ml 3-necked round bottom flask fitted with a condenser and thermometer and magnetically stirred, was added 12.97 g (0.063 mole) of 4,5-dimethoxy-7-indanaldehyde, 3.00 g (0.039 mole) of ammonium acetate, 13.0 ml (0.292 mole) of CH3NO2 and 40 ml of glacial acetic acid. This mixture was heated for 1 to 2 hours at 112°C. As the reaction solution began to cool the entire solution solidified. After cooling in an ice bath and removing the solvent by filtration, the solid 4,5-dimethoxy-7-nitrovinylindane was washed with a small volume of acetic acid giving fine yellow needles (9.55 g) after thorough drying. The filtrate was poured into 300 ml of ice and water from which precipitated a slightly gummy, yellow-brown solid. This gave an additional 1.43 g of crystalline solid after drying and crystallizing from methanol giving a total yield of 10.98 g (70%). An analytical sample melted at 128°-130°C. Anal. Calcd. For C13H15NO4 : C, 62.64; H, 6.06; N, 5.62. Found: C, 62.79; H, 6.12; N, 5.52.

Provenance & Evidence