Potassium Carbonate → 1-Bromo-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid methyl ester

HRID 2253109Notes

Reaction equation

HRID 2253109 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([S:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:10]=2)[C:5]([OH:19])=[C:4]([C:20]([OH:22])=[O:21])[N:3]=1.[C:23](=O)([O-])[O-].[K+].[K+].S([O-])(OC)(=O)=O>CC(C)=O>[CH3:23][O:21][C:20]([C:4]1[N:3]=[C:2]([Br:1])[C:11]2[C:6]([C:5]=1[OH:19])=[CH:7][CH:8]=[C:9]([S:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:10]=2)=[O:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4694097Methyl sulfate(1-)HCID 860145681-Bromo-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid

Product 1

HCID 865954711-Bromo-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid methyl esterYield 92.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Bromo-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid (10.0 g), potassium carbonate (3.7 g) and methyl sulfate (3.4 g) were suspended in 500 ml acetone and stirred at reflux overnight. Reaction mixture was concentrated and residue partitioned between 1 N hydrochloric acid and ethyl acetate. Organic layer was dried over magnesium sulfate and filtered. Filtrate concentrated to give title compound (9.6 g). MS-(+)-ion M+1=389.9, 391.9.

Workup

  1. temperatureat reflux overnight
  2. customReaction mixture
  3. concentrationwas concentrated
  4. customresidue partitioned between 1 N hydrochloric acid and ethyl acetate
  5. dry with materialOrganic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationFiltrate concentrated

Sources & evidence

ORD record
ord-b9fea723ecb94f9b93cd38bf790a8992
Source dataset
uspto-grants-2008_01
Patent number
US07323475B2

Reaction notes

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