تفاعل #46570

معادلة التفاعل

methylamine

H2O

2-(bromomethyl)naphthalene

→

title compound

المردود 54.0%

2-(methylaminomethyl)naphthalene

المردود 54.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   تركيزwas then concentrated under vacuum
2. 2
   غسيلwashed with 1.0 N NaOH
3. 3
   تجفيفwith brine, dried (Na2SO4)
4. 4
   تركيزconcentrated to dryness
5. 5
   أخرىPurification by flash chromatography on silica gel (98:2 to 9:1 CHCl3/methanol containing 5% NH4OH)

الإجراء التجريبي

To a stirred solution of 40 wt % methylamine in H2O (50 mL, 581 mmole) in THF (50 mL) at 0° C. was added 2-(bromomethyl)naphthalene (10 g, 43 mmole) in one portion. The reaction was allowed to warm to RT and stirred for 16 hr, then was then concentrated under vacuum. The residue was taken up in Et2O and washed with 1.0 N NaOH then with brine, dried (Na2SO4), and concentrated to dryness. Purification by flash chromatography on silica gel (98:2 to 9:1 CHCl3/methanol containing 5% NH4OH) gave the title compound (3.95 g, 54%) as a clear oil: 1H NMR (400 MHz, CDCl3) δ 7.85 (m, 3 H), 7.79 (s, 1 H), 7.49 (m, 3 H), 3.94 (s, 2 H), 2.53 (s, 3 H).

المصدر