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N-(2,2-dimethylpropyl)-6-methylpyridin-2-amine synthesis

4synthesis methods
-

Yield:1250716-30-3 107 g

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 0 - 60; for 2 h;Inert atmosphere;

Steps:

245.10 Step 10) N-(2,2-dimethylpropyl)-6-methylpyridin-2-amine

Under a nitrogen atmosphere, to a suspension of lithium aluminum hydride (65.0 g) in THF (1.5 L) was added a solution of 2,2-dimethyl-N-(6-methylpyridin-2-yl)propanamide (110 g) in THF (1.5 L) at 0° C., and the mixture was stirred at 60° C. for 2 hr. To the reaction solution were successively added water (65 mL), 4N aqueous sodium hydroxide solution (65 mL) and water (195 mL) at 0° C., and the resulting white precipitate was removed by filtration. The solvent in the filtrate was evaporated under reduced pressure to give the title compound (107 g) as a colorless oil. (1296) 1H NMR (400 MHz, DMSO): δ 0.89 (9H, s), 2.20 (3H, s), 3.05-3.07 (2H, d, J=6.4 Hz), 6.14 (1H, s), 6.24-6.26 (1H, d, J=6.8 Hz), 6.29-6.31 (1H, d, J=8.4 Hz), 7.16-7.20 (1H, m).

References:

US2016/115128,2016,A1 Location in patent:Paragraph 1295; 1296