HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 250499
Notes
Print preview

Reaction equation

HRID 250499 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 180Acetone
Solvent

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-333fe94e0a984057a4091d4cb9e58869
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07863292B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes