Réaction #1688223

Équation de réaction

6-bromo-3,4-dihydro-1(1H)-isoquinolinone

6-Bromo-3,4-dihydro-1(1H)-isoquinolinone

MeOH

→

title compound

6-bromo-1,2,3,4-tetrahydroisoquinoline

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   Températureat reflux for 20 h
2. 2
   Autrethe solvent removed
3. 3
   Températurethe residue heated with 2N HCl for 3 h
4. 4
   TempératureThe reaction was cooled
5. 5
   Extractionextracted with CH2Cl2
6. 6
   Autredried
7. 7
   Autreevaporated

Mode opératoire

A solution of 6-bromo-3,4-dihydro-1(1H)-isoquinolinone (Example 31, Step 1; 5.5 g, 1.0 mmol) in THF (25 mL) was treated with 1M BH3 in THF (5 mL, 5 mmol) and heated at reflux for 20 h. To the mixture was added MeOH (5 mL), the solvent removed and the residue heated with 2N HCl for 3 h. The reaction was cooled, made basic with aqueous NH4OH and extracted with CH2Cl2, dried and evaporated to give the title compound as a gum which was used as such.

Source