反応 #1978434

反応方程式

Sodium hydride

3-bromopropane

6-bromo-3,4-dihydroisoquinolin-1(2H)-one

6-Bromo-3,4-dihydroisoquinolin-1(2H)-one

→

6-bromo-2-propyl-3,4-dihydroisoquinolin-1(2H)-one

収率 71.1%

6-Bromo-2-propyl-3,4-dihydroisoquinolin-1(2H)-one

収率 71.1%

溶媒

DMF

DMF

DMF

反応条件

後処理

1. 1
   workup.ADDITIONOnce addition
2. 2
   温度then heated at 60° C. for 4hrs
3. 3
   温度The reaction mixture was cooled
4. 4
   その他quenched with water
5. 5
   抽出extracted three times with diethyl ether
6. 6
   洗浄The combined organics were washed with brine
7. 7
   乾燥dried (MgSO4)
8. 8
   その他evaporated to dryness
9. 9
   その他The residue was purified on silica eluting with 30-100% EtOAc/heptane

実験手順

Sodium hydride (60% w/w suspension in oil) (1.17 mmol, 46.7 mg) was suspended in DMF (0.5 ml) under argon. The mixture was cooled to 0° C. before dropwise addition of 6-bromo-3,4-dihydroisoquinolin-1(2H)-one (1K2) (1.06 mmol, 240 mg) in DMF (1.5 ml) The reaction was stirred at 0° C. for 30 min before addition of 3-bromopropane (1K3) (1.592 mmol, 196 mg) in DMF (1 ml). Once addition was complete the reaction was allowed to warm to room temperature then heated at 60° C. for 4hrs. The reaction mixture was cooled, quenched with water and extracted three times with diethyl ether. The combined organics were washed with brine, dried (MgSO4) and evaporated to dryness. The residue was purified on silica eluting with 30-100% EtOAc/heptane to give 6-bromo-2-propyl-3,4-dihydroisoquinolin-1(2H)-one (1K4) 202 mg (70.9%); 1H NMR (400 MHz, CDCl3) δ 7.94 (d, 1H) 7.47 (d, 1H) 7.33 (s, 1H) 3.54 (m, 4H) 2.96 (t, 2H) 1.65 (m, 2H) 0.96 (t, 3H).

出典