Benzoyl Peroxide → HCID 86617077, compound

HRID 706198Notes

Reaction equation

HRID 706198 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20])=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:46]N1C(=O)CCC1=O>C1C=CC=CC=1>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([Br:46])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20])=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 667135276-Benzenesulfonyl-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester

Product 1

HCID 86617077HCID 86617077, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a mixture of 6-benzenesulfonyl-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester (100 mg, 0.26 mmol; see U.S. Patent Application Publication No. 2004/0254215) and benzene (4.5 mL) was added benzoyl peroxide (6.3 mg, 0.026 mmol). Resulting mixture was refluxed for 15 min. prior to the addition of N-bromosuccinimide (51 mg, 0.29 mmol). Reaction mixture was refluxed overnight. It was concentrated and the crude product was purified by silica gel chromatography (eluting with 20%-80%) ethyl acetate/hexanes to provide the title compound (91 mg). MS-(+)-ion: M+1=466.18, 464.14.

Workup

  1. customResulting mixture
  2. temperaturewas refluxed for 15 min.
  3. customReaction mixture
  4. temperaturewas refluxed overnight
  5. concentrationIt was concentrated
  6. customthe crude product was purified by silica gel chromatography (eluting with 20%-80%) ethyl acetate/hexanes

Sources & evidence

ORD record
ord-02ab175116384331a588d5128ff4b242
Source dataset
uspto-grants-2015_11
Patent number
US09174976B2

Reaction notes

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