Dimethyl Sulfate → N-(4-methoxy-2-methylquinolin-6-yl)acetamide

HRID 2187590Notes

Reaction equation

HRID 2187590 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12][C:13](=[O:15])[CH3:14])[CH:10]=2)[N:5]=[C:4]([CH3:16])[CH:3]=1.S(OC)(O[CH3:21])(=O)=O>C1(C)C=CC=CC=1>[CH3:21][O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12][C:13](=[O:15])[CH3:14])[CH:10]=2)[N:5]=[C:4]([CH3:16])[CH:3]=1

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 178474057HCID 178474057, compound

Product 1

HCID 4785621N-(4-methoxy-2-methylquinolin-6-yl)acetamideYield 52.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of N-(4-hydroxy-2-methyl-6-quinolyl)acetamide (100 g, 0.46 mol) obtained in Preparation Example 1-1, Step 2 in toluene (490 ml) was added dimethyl sulfate (75 ml, 0.79 mol) and the mixture was refluxed under heating for 8 hr. The resulting precipitate was collected by filtration, dissolved in water (1350 ml) and heated to 70° C. The solution was filtered and 35% aqueous sodium hydroxide solution (100 ml) was added to the filtrate. The resulting precipitate was collected by filtration to give N-(4-methoxy-2-methyl-6-quinolyl)acetamide (55.3 g, 52%, pale-brown crystals).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 8 hr
  3. filtrationThe resulting precipitate was collected by filtration
  4. dissolutiondissolved in water (1350 ml)
  5. filtrationThe solution was filtered
  6. addition35% aqueous sodium hydroxide solution (100 ml) was added to the filtrate
  7. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-659903a2355b4dbfb7c05be6698fde4c
Source dataset
uspto-grants-2002_06
Patent number
US06410561B1

Reaction notes

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