Reaktion #1978434

Reaktionsgleichung

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

Ausbeute 71.1%

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

Ausbeute 71.1%

Lösungsmittel

DMF

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONOnce addition
2. 2
   Temperaturthen heated at 60° C. for 4hrs
3. 3
   TemperaturThe reaction mixture was cooled
4. 4
   Sonstigequenched with water
5. 5
   Extraktionextracted three times with diethyl ether
6. 6
   WaschenThe combined organics were washed with brine
7. 7
   Trocknendried (MgSO4)
8. 8
   Sonstigeevaporated to dryness
9. 9
   SonstigeThe residue was purified on silica eluting with 30-100% EtOAc/heptane

Vorschrift

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).

Quelle