Réaction #1978434

Équation de réaction

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

Rendement 71.1%

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

Rendement 71.1%

Solvants

DMF

DMF

DMF

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONOnce addition
2. 2
   Températurethen heated at 60° C. for 4hrs
3. 3
   TempératureThe reaction mixture was cooled
4. 4
   Autrequenched with water
5. 5
   Extractionextracted three times with diethyl ether
6. 6
   LavageThe combined organics were washed with brine
7. 7
   Séchagedried (MgSO4)
8. 8
   Autreevaporated to dryness
9. 9
   AutreThe residue was purified on silica eluting with 30-100% EtOAc/heptane

Mode opératoire

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).

Source