ChemicalBook--->CAS DataBase List--->3749-21-1

3749-21-1

3749-21-1 Structure

3749-21-1 Structure
IdentificationBack Directory
[Name]

4-BROMO-ISOQUINOLINE 2-OXIDE
[CAS]

3749-21-1
[Synonyms]

Fampridine Impurity 58
4-Bromoisoquinoline N-oxide
4-BROMO-ISOQUINOLINE 2-OXIDE
Isoquinoline, 4-bromo-, 2-oxide
4-bromo-2-oxidoisoquinolin-2-ium
[Molecular Formula]

C9H6BrNO
[MDL Number]

MFCD00234486
[MOL File]

3749-21-1.mol
[Molecular Weight]

224.05
Chemical PropertiesBack Directory
[storage temp. ]

under inert gas (nitrogen or Argon) at 2-8°C
Hazard InformationBack Directory
[Synthesis]

4-Bromoisoquinoline

1532-97-4

4-BROMO-ISOQUINOLINE 2-OXIDE

3749-21-1

General procedure for the synthesis of 4-bromoisoquinoline 2-oxide from 4-bromoisoquinoline (Compound 13A): a chloroform (100 mL) solution of 4-bromoisoquinoline (4.16 g, 18.6 mmol) was added dropwise to a chloroform (100 mL) solution of 70% mCPBA (12.4 g, 50.3 mmol) over a period of 1 h at room temperature. The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was washed with 1N NaOH solution (2 x 150 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give an off-white solid compound 13A (4.23 g, 94% yield).1H NMR (400 MHz, CDCl3) δ 8.71 (s, 1 H), 8.43 (s, 1 H), 8.09 (d, 1 H) , J = 8 Hz), 7.70 (m, 3H).

[References]

[1] Patent: US2004/19063, 2004, A1
[2] Patent: US2004/181064, 2004, A1
[3] Journal of Medicinal Chemistry, 1995, vol. 38, # 21, p. 4234 - 4243
[4] Chemical Communications, 2018, vol. 54, # 32, p. 3977 - 3980
[5] Organic and Biomolecular Chemistry, 2016, vol. 14, # 24, p. 5820 - 5825
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