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

HRID 1432201Notes

Reaction equation

HRID 1432201 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-0318bfcf3ecc480581a74ea719c5f810
Source dataset
uspto-grants-2009_11
Patent number
US07612080B2

Reaction notes

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