Sodium Hydroxide → Isoquinoline, 5-bromo-, 2-oxide

HRID 1403073Notes

Reaction equation

HRID 1403073 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Br:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH:15]=[CH:16][N:17]=[CH:18]2.[OH-].[Na+]>C(Cl)(Cl)Cl>[Br:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH:15]=[CH:16][N+:17]([O-:9])=[CH:18]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 7364875-Bromoisoquinoline

Product 1

HCID 22665708Isoquinoline, 5-bromo-, 2-oxideYield 52.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Aqueous meta-chloroperbenzoic acid (65%, 29 g) was added to a solution of 5-bromoisoquinoline (20.7 g) in chloroform (250 ml), and the mixture was stirred at room temperature for 1 hour. The reaction solution was neutralized with an aqueous sodium hydroxide solution with cooling in an ice bath and partitioned into organic and aqueous layers. The organic layer was washed with brine. The organic layer thus washed was dried over anhydrous sodium sulfate. Then, the solvent was distilled off, and small amounts of chloroform and diethyl ether were added to the residue. The deposit was filtrated to obtain compound (1a) (11.8 g, 50%).

Workup

  1. temperaturewith cooling in an ice bath
  2. custompartitioned into organic and aqueous layers
  3. washThe organic layer was washed with brine
  4. washThe organic layer thus washed
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. distillationThen, the solvent was distilled off
  7. additionsmall amounts of chloroform and diethyl ether were added to the residue
  8. filtrationThe deposit was filtrated

Sources & evidence

ORD record
ord-f714c9113ea54a8bbdd64dd7f5f651db
Source dataset
uspto-grants-2014_12
Patent number
US08912181B2

Reaction notes

Loading…