Sodium Hydroxide → 6-Bromo-3,4-dihydro-2H-isoquinolin-1-one

HRID 2377003Notes

Reaction equation

HRID 2377003 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+].[OH-].[Na+]>S(=O)(=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

5

Reactant 3

HCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 5206955-Bromo-1-indanone

Product 1

HCID 218654506-Bromo-3,4-dihydro-2H-isoquinolin-1-oneYield 7%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 5-bromo-1-indanone (15 g, 71 mmol) in concentrated sulfuric acid (75 mL) was cooled to 0° C. Sodium azide (6.5 g, 100 mmol) was added portionwise over 1 hour. The reaction was allowed to warm to room temperature and stirred for 24 hours. The mixture was poured onto ice, neutralised with 4N sodium hydroxide and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by dry flash chromatography using 50-100% ethyl acetate/isohexane to give 6-bromo-3,4-dihydroisoquinolin-1(2H)-one (1.1 g, 7%). δH (500 MHz, CDCl3): 7.92 (1H, d, J=8.3 Hz), 7.49 (1H, dd, J=1.4, 8.3 Hz), 7.39 (1H, d, J=0.9 Hz), 6.46 (1H, s), 3.57-3.55 (2H, m), 2.98 (2H, t, J=6.6 Hz).

Workup

  1. temperatureto warm to room temperature
  2. additionThe mixture was poured onto ice
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified
  8. customby dry flash chromatography

Sources & evidence

ORD record
ord-4978583b8fea491daeb5637af7a9808a
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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