Methanol → 6-Bromo-1,2,3,4-tetrahydroisoquinoline

HRID 1601041Notes

Reaction equation

HRID 1601041 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[NH:7][CH2:6][CH2:5]2.CO>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][NH:7][CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 887MethanolHCID 218654506-Bromo-3,4-dihydro-2H-isoquinolin-1-one

Product 1

HCID 158851836-Bromo-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  1. temperatureat reflux for 20 h
  2. customthe solvent removed
  3. temperaturethe residue heated with 2N HCl for 3 h
  4. temperatureThe reaction was cooled
  5. extractionextracted with CH2Cl2
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-35c7fdf93afe41d6a3b417e402592e04
Source dataset
uspto-grants-1999_11
Patent number
US05977134

Reaction notes

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