Hydrogen Peroxide → HCID 14221252, compound

HRID 511318Notes

Reaction equation

HRID 511318 reaction equation
S(C1C=CC(C)=CC=1)([O-])(=O)=[O:2].[Br:12][C:13]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[C:19]2[C:14]=1[CH:15]=[CH:16][N+:17]([CH3:26])=[CH:18]2.C([O-])([O-])=O.[Na+].[Na+].OO>C(Cl)Cl>[Br:12][C:13]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[C:19]2[C:14]=1[CH:15]=[CH:16][N:17]([CH3:26])[C:18]2=[O:2]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 12999505HCID 12999505, compound

Product 1

HCID 14221252HCID 14221252, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-2-methyl-8-nitroisoquinolinium tosylate (20.0 g) in CH2Cl2 (400 mL) was added aq. Na2CO3 (5%, 400 mL) and hydrogen peroxide (30%, 20 mL). The resulting mixture was stirred at room temperature for 16 h, the organic layer was separated and the aqueous layer was extracted with CH2Cl2 (5×100 mL). The combined organic layer was washed with water (100 mL), dried over sodium sulfate and evaporated to give the crude product, which was purified by column chromatography on silica gel (EtOAc/CH2Cl2 (1:9)) to give 2.2 g of the desired product (yield: 8%). 1H NMR (CDCl3, 300 MHz): δ=3.60 (s, 3 H), 6.90 (d, J=7.8 Hz, 1 H), 7.28 (d, J=7.2 Hz, 1 H), 7.30 (d, J=7.2 Hz, 1 H), 7.92 (d, J=7.8 Hz, 1 H).

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous layer was extracted with CH2Cl2 (5×100 mL)
  3. washThe combined organic layer was washed with water (100 mL)
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customto give the crude product, which
  7. customwas purified by column chromatography on silica gel (EtOAc/CH2Cl2 (1:9))

Sources & evidence

ORD record
ord-b9cb7d4987b84617a84984a2b6ee9ab1
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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