Ethyl Acetate → 6-Bromo-3,4-dihydro-2H-isoquinolin-1-one

HRID 1601040Notes

Reaction equation

HRID 1601040 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[N-:12]=[N+]=[N-].[Na+].CCOC(C)=O>C1C=CC=CC=1.OS(O)(=O)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[NH:12][CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 5206955-Bromo-1-indanone

Product 1

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

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1118Sulfuric AcidSolvent

Procedure

To a rapidly stirred solution of 5-bromo-1-indanone (Aldrich) (15.0 g, 71.1 mmol) in benzene (200 mL) and H2SO4 (38 mL) was added NaN3 portionwise over 20 minutes. The mixture was diluted EtOAc, washed with water then brine, dried and evaporated. Chromatography of the residue (silica gel; hexane/EtOAc 1:1) afforded the title compound as a solid.

Workup

  1. washwashed with water
  2. dry with materialbrine, dried
  3. customevaporated

Sources & evidence

ORD record
ord-782834aa3f864175b5be9043811d99ec
Source dataset
uspto-grants-1999_11
Patent number
US05977134

Reaction notes

Loading…