Dimethyl Sulfate → HCID 178439762, compound

HRID 522366Notes

Reaction equation

HRID 522366 reaction equation
S(OC)(O[CH3:5])(=O)=O.[CH2:8]([C:11]1[C:12]([OH:22])=[N:13][C:14]2[C:19]([C:20]=1[OH:21])=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:9]=[CH2:10].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:5][O:21][C:20]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[C:12]([OH:22])[C:11]=1[CH2:8][CH:9]=[CH2:10]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 178439761HCID 178439761, compound

Product 1

HCID 178439762HCID 178439762, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dimethyl sulfate (0.237 ml) was added to a mixture of 3-(prop-2-en-1-yl)quinoline-2,4-diol (1.0 g) and potassium carbonate (1.37 g) in acetone (100 ml) and the mixture was stirred at room temperature for 3 hours then warmed to 40° C. for 30 minutes. The reaction mixture was cooled and the solids were removed by filtration. The filtrate was concentrated in vacuo. Purification by flash chromatography (ISCO, 4-10% acetone/DCM) gave the desired product (0.70 g). LRMS (ES+) M/Z (M+H)+ 216.0.

Workup

  1. temperaturethen warmed to 40° C. for 30 minutes
  2. temperatureThe reaction mixture was cooled
  3. customthe solids were removed by filtration
  4. concentrationThe filtrate was concentrated in vacuo
  5. customPurification by flash chromatography (ISCO, 4-10% acetone/DCM)

Sources & evidence

ORD record
ord-251e73f3587e4064ad592745519f19d8
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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