Acetic Acid → 6-Bromoisoquinoline 2-oxide

HRID 1067230Notes

Reaction equation

HRID 1067230 reaction equation
C(O)(=[O:3])C.OO.C(OO)(=O)C.[Br:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[N:18][CH:17]=[CH:16]2>O>[Br:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[N+:18]([O-:3])[CH:17]=[CH:16]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 6585Peracetic AcidHCID 3136816-Bromoisoquinoline

Product 1

HCID 222501786-Bromoisoquinoline 2-oxide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Acetic acid (8 mL) and 30% hydrogen peroxide (4 mL) were heated at 80° C. for 1 h. The cooled solution of peracetic acid was added to 6-bromoisoquinoline (Tyson, F. T. J. Am. Chem. Soc., 1939, 61, 183) (0.389 g, 1.87 mmol) and the mixture was then heated at 80° C. for 18 h. The mixture was diluted with water (15 mL) and concentrated in vacuo to ca. half the volume and the residue was extracted with CH2Cl2 (2×25 mL). The combined organics were washed with saturated aqueous NaHCO3 (25 mL), dried over MgSO4 and evaporated to leave an oil. Azeotroping with PhMe (×3) and then CH2Cl2 (×3) gave 6-bromoisoquinoline N-oxide (0.420 g, quant) as a cream-coloured solid. 1H (δ, CDCl3, 300 MHz) 7.6-7.65 (2H, m), 7.77 (1H, dd), 8.0 (1H, s), 8.2 (1H, dd), 8.85 (1H, s);

Workup

  1. concentrationconcentrated in vacuo to ca. half the volume
  2. extractionthe residue was extracted with CH2Cl2 (2×25 mL)
  3. washThe combined organics were washed with saturated aqueous NaHCO3 (25 mL)
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customto leave an oil
  7. customAzeotroping with PhMe (×3)

Sources & evidence

ORD record
ord-5a2efed2af3142ae9403dda814d11aff
Source dataset
uspto-grants-2001_06
Patent number
US06248738B1

Reaction notes

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