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

HRID 1170720Notes

Reaction equation

HRID 1170720 reaction equation
S(OC)(O[CH3:5])(=O)=O.[OH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:20](=[O:22])[CH3:21])[CH:17]=2)[N:12]=[C:11]([CH3:23])[CH:10]=1>C1(C)C=CC=CC=1>[CH3:5][O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:20](=[O:22])[CH3:21])[CH:17]=2)[N:12]=[C:11]([CH3:23])[CH:10]=1

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 178474057HCID 178474057, compound

Product 1

HCID 4785621N-(4-methoxy-2-methylquinolin-6-yl)acetamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Dimethyl sulfate (294 g, 2.33 mol) was charged to a suspension of hydroxyquinoline 4 (287 g, 1.33 mol) in toluene (1.5 L) and the mixture was refluxed for 6 h. After cooling to ambient temperature, the resulting dark yellow solids were collected by filtration and washed with toluene. The dry solid was dissolved in water (2.5 L) and the pH adjusted to 14 using 35% aqueous NaOH (290 g). The resulting tan precipitate was collected by filtration, washed with copious amounts of water and dried in vacuo at 60° C. to give methoxyquinoline 5 as light tan solid (259 g, 85% yield); 1H NMR (DMSO) δ 10.18 (s, 1H), 8.46 (s, 1H), 7.76 (m, 2H), 6.84 (s, 1H), 3.99 (s, 3H), 2.55 (s, 3H), 2.09 (s, 3H); 13C NMR (DMSO) δ 168.36, 160.99, 158.07, 144.86, 135.87, 128.27, 122.78, 119.26, 108.80, 101.20, 55.69, 25.08, 23.97.

Workup

  1. temperaturethe mixture was refluxed for 6 h
  2. filtrationthe resulting dark yellow solids were collected by filtration
  3. washwashed with toluene
  4. dissolutionThe dry solid was dissolved in water (2.5 L)
  5. filtrationThe resulting tan precipitate was collected by filtration
  6. washwashed with copious amounts of water
  7. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-8d5577b02a1643c3886da2fc0ee59a61
Source dataset
uspto-grants-2010_11
Patent number
US07826982B2

Reaction notes

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