Sodium Hydroxide → HCID 57486961, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring suspension of lithium aluminum hydride (1.63 g, 42.8 mmol, 6.0 equiv) in THF (15 mL) at 0° C. was added a solution of 1,4-dimethoxy-2,3,5-trimethyl-6-(2-nitrovinyl)benzene (1.8 g, 7.14 mmol) in THF (15 mL) over 30 min. Following addition, the mixture was warmed to 60° C. and stirred for 2 hr. After this time, the reaction was deemed complete by HPLC analysis, the mixture was slowly transferred to 100 mL 6M aqueous sodium hydroxide and stirred for 20 min. The resulting suspension was filtered in vacuo and the cake rinsed with i-propyl acetate (200 mL). The organics were removed and the remaining aqueous layer was extracted 2× with i-propyl acetate (200 mL), combined, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give 1.6 g of light brown oil, which solidified on standing to give crude amine 2-(2,5-dimethoxy-3,4,6-trimethylphenyl)ethanamine.1H NMR (CDCl3, 400 MHz) 3.63 (s, 3H), 3.59 (s, 3H), 2.79 (m, 2H), 2.63 (m, 2H), 2.20 (s, 3H), 2.15 (s, 3H) ppm.

Provenance & Evidence