반응 #1978434

반응 방정식

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

수율 71.1%

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

수율 71.1%

용매

DMF

DMF

DMF

반응 조건

후처리

1. 1
   workup.ADDITIONOnce addition
2. 2
   온도then heated at 60° C. for 4hrs
3. 3
   온도The reaction mixture was cooled
4. 4
   기타quenched with water
5. 5
   추출extracted three times with diethyl ether
6. 6
   세척The combined organics were washed with brine
7. 7
   건조dried (MgSO4)
8. 8
   기타evaporated to dryness
9. 9
   기타The residue was purified on silica eluting with 30-100% EtOAc/heptane

실험 절차

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).

출처