تفاعل #1978434

معادلة التفاعل

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

المردود 71.1%

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

المردود 71.1%

المذيبات

DMF

DMF

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONOnce addition
2. 2
   درجة الحرارةthen heated at 60° C. for 4hrs
3. 3
   درجة الحرارةThe reaction mixture was cooled
4. 4
   أخرىquenched with water
5. 5
   استخلاصextracted three times with diethyl ether
6. 6
   غسيلThe combined organics were washed with brine
7. 7
   تجفيفdried (MgSO4)
8. 8
   أخرىevaporated to dryness
9. 9
   أخرىThe residue was purified on silica eluting with 30-100% EtOAc/heptane

الإجراء التجريبي

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).

المصدر