2-Methoxyaniline → N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)-2-methoxyaniline
Reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:17][CH:18]1[O:22][CH:21]([CH3:23])[CH:20]([CH3:24])[O:19]1>>[CH3:24][CH:20]1[CH:21]([CH3:23])[O:22][CH:18]([CH2:17][NH:5][C:4]2[CH:6]=[CH:7][CH:8]=[CH:9][C:3]=2[O:2][CH3:1])[O:19]1Participants
4
Conditions
- Temperature
- 100 °C
Procedure
2-Methoxyaniline (87 ml; 0.7 mole) and sodium carbonate (31.66 grams) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. 2-Bromomethyl-4,5-dimethyl-1,3-dioxolane (25 mls) was added and the reaction mixture was heated at a temperature of 100° C. for a period of about 4 hours. After this time the reaction mixture was filtered and additional sodium carbonate (5.00 grams) was added to the filtrate. The mixture was then distilled under reduced pressure to yield the desired product N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)-2-methoxyaniline boiling at 125° to 128° C. at 0.1 mm of Hg pressure.