Dimethyl Sulfate → HCID 19788691, compound

HRID 1609051Notes

Reaction equation

HRID 1609051 reaction equation
[F:1][C:2]1[C:11]([F:12])=[CH:10][C:9]2[C:13](=[O:21])[C:14]([C:16]([O:18][CH2:19]C)=[O:17])=[CH:15][N:7]3[C:8]=2[C:3]=1[CH2:4][CH2:5][NH:6]3.[CH3:22]OS(OC)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>O>[F:1][C:2]1[C:11]([F:12])=[CH:10][C:9]2[C:13](=[O:21])[C:14]([C:16]([O:18][CH3:19])=[O:17])=[CH:15][N:7]3[C:8]=2[C:3]=1[CH2:4][CH2:5][N:6]3[CH3:22]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 20083163HCID 20083163, compound

Product 1

HCID 19788691HCID 19788691, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 9.5 g (33 mmol) of pyridocinnoline (5) obtained in Example 1, 95 ml of dimethylsulfate was added, and the mixture was heated at 100° to 120° C. for 8 hours. After air-cooled, the solution was added to 900 ml of water containing 137 g of anhydrous potassium carbonate, and the solution was stirred at room temperature for 30 minutes. The solution was extracted with 800 ml of chloroform and after drying over magnesium sulfate, the solvent was removed by distillation. The residue was purified by silica gel chromatography (250 g of silica gel, eluent solvent: chloroform), and the obtained crystal was filtered off and washed with ether to obtain 5.3 g of the subject compound (6) in a 56% yield. The result of the analysis of this compound was as follows.

Workup

  1. temperaturethe mixture was heated at 100° to 120° C. for 8 hours
  2. temperatureAfter air-cooled
  3. extractionThe solution was extracted with 800 ml of chloroform
  4. dry with materialafter drying over magnesium sulfate
  5. customthe solvent was removed by distillation
  6. customThe residue was purified by silica gel chromatography (250 g of silica gel, eluent solvent: chloroform)
  7. filtrationthe obtained crystal was filtered off
  8. washwashed with ether

Sources & evidence

ORD record
ord-50fa823207cd4aa5883cca7c94f29ed3
Source dataset
uspto-grants-1995_03
Patent number
US05399553

Reaction notes

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