反応 #487497

反応方程式

2-amino-6-methoxybenzoic acid

benzylamine

diisopropylethylamine

2-chloro-1,3-dimethylimidazolinium chloride

→

2-Amino-N-benzyl-6-methoxybenzamide

収率 46.3%

溶媒

water

dichloromethane

反応条件

後処理

1. 1
   抽出extracted with dichloromethane
2. 2
   洗浄The organic solution was successively washed with aqueous saturated NaHCO3 and water
3. 3
   乾燥The organic layer was dried over MgSO4
4. 4
   その他the solvent was removed by rotary evaporator
5. 5
   その他The residue was purified by column chromatography (silica gel, 2% 2.0 M ammonia MeOH solution in CH2Cl2)

実験手順

To a solution of 2-amino-6-methoxybenzoic acid (0.841 g, 5.0 mmol, 1.0 equiv), benzylamine (0.643 g, 6.0 mmol, 1.2 equiv), and diisopropylethylamine (1.935 g, 15.0 mmol, 3.0 equiv) in 50 mL of dichloromethane was added 2-chloro-1,3-dimethylimidazolinium chloride (1.099 g, 6.5 mmol, 1.3 equiv) at room temperature. The mixture was stirred at room temperature for 6 hours, poured into water, and extracted with dichloromethane. The organic solution was successively washed with aqueous saturated NaHCO3 and water. The organic layer was dried over MgSO4 and the solvent was removed by rotary evaporator. The residue was purified by column chromatography (silica gel, 2% 2.0 M ammonia MeOH solution in CH2Cl2) to give 2-Amino-N-benzyl-6-methoxybenzamide (0.593 g, 46%) as a solid. 1H NMR (400 MHz, CHLOROFORM-d) δ 3.81 (s, 3H), 4.62 (s, 1H), 4.63 (s, 1H), 6.07 (vb.s., 2H), 6.19 (d, J=8.2 Hz, 1H), 6.32 (d, J=8.2 Hz, 1H), 7.07 (t, J=8.2 Hz, 1H), 7.14-7.54 (m, 5H), 8.05 (br. s., 1H); HPLC: tR=4.72 min, UV254=99%; HRMS (ESI): m/z calcd for C15H16N2O2 [M+1]+257.1296. Found 257.1294.

出典