Dimethyl Sulfate → HCID 67347512, compound

HRID 1669392Notes

Reaction equation

HRID 1669392 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:13](=[O:28])[CH:14]=[CH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH:17]=2)[C:3]1=[O:29].[CH3:30]N(C)P(N(C)C)(N(C)C)=O.[H-].[Na+].S(OC)(OC)(=O)=O>O>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:30])=[C:4]([C:13](=[O:28])[CH:14]=[CH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH:17]=2)[C:3]1=[O:29]

Participants

6

Reactant 4

HCID 6497Dimethyl SulfateHCID 12679HexamethylphosphoramideHCID 24758Sodium hydrideHCID 67346190HCID 67346190, compound

Product 1

HCID 67347512HCID 67347512, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 0.55 g of 1-methyl-4-hydroxy-3-[3-[3-[(methoxycarbonyl)methoxy]phenyl]-1-oxo-2-propenyl]-2(1H)-quinolinone and 5 ml of hexamethylphosphoramide was added 67 mg of sodium hydride (60% oily) under ice-cooling. After stirred at room temperature for 1 hour, 0.2 ml of dimethyl sulfate was added, and this was stirred at room temperature for 3 hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. After dried over anhydrous sodium sulfate, the extract was concentrated under reduced pressure, and the resulting residue was subjected to silica column gel chromatography to obtain 0.21 g of 1-methyl-4-methoxy-3-[3-[3-[(methoxycarbonyl)methoxy]phenyl]-1-oxo-2-propenyl]-2(1H)-quinolinone [Compound No. (60e)] as a yellow crystal.

Workup

  1. temperaturecooling
  2. stirringthis was stirred at room temperature for 3 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialAfter dried over anhydrous sodium sulfate
  5. concentrationthe extract was concentrated under reduced pressure

Sources & evidence

ORD record
ord-51b929a200f14b888335823aac8801de
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

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