N-ethoxycarbonyl-m-bromophenethylamine → 6-Bromo-3,4-dihydro-2H-isoquinolin-1-one

HRID 1741701Notes

Reaction equation

HRID 1741701 reaction equation
C([O:3][C:4]([NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Br:15])[CH:10]=1)=O)C>O>[Br:15][C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[C:4](=[O:3])[NH:6][CH2:7][CH2:8]2

Participants

3

Reactant 1

HCID 18963948N-ethoxycarbonyl-m-bromophenethylamine

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of N-ethoxycarbonyl-m-bromophenethylamine (6.87 g, 25.25 mmol) in polyphosphoric acid (50 mL) is heated to reflux for 5 min. When the mixture cools, H2O is added and the resulting solution extracted with EtOAc (1×300 ml). The organic phase is dried and concentrated in vacuo and the residue chromatographed (silica gel, EtOAc) to give 6-bromo-1-oxo-1,2,3,4-tetrahydroisoquinoline.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 5 min
  3. extractionthe resulting solution extracted with EtOAc (1×300 ml)
  4. customThe organic phase is dried
  5. concentrationconcentrated in vacuo
  6. customthe residue chromatographed (silica gel, EtOAc)

Sources & evidence

ORD record
ord-c684491e372b43aaacf1cffd7ab3d91b
Source dataset
uspto-grants-1994_08
Patent number
US05334600

Reaction notes

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