Dimethylformamide → Methyl 6-[(4,6-Dimethoxypyrimidin-2-yl)oxy]quinolin-5-carboxylate

HRID 52008

Reaction equation

HRID 52008 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:3]=1[C:12]([O:14][CH3:15])=[O:13].[CH3:16][O:17][C:18]1[CH:23]=[C:22]([O:24][CH3:25])[N:21]=[C:20](S(C)(=O)=O)C=1.C(=O)([O-])[O-].[K+].[K+].C[N:37](C)C=O>>[CH3:16][O:17][C:18]1[CH:23]=[C:22]([O:24][CH3:25])[N:21]=[C:20]([O:1][C:2]2[CH:11]=[CH:10][C:9]3[N:8]=[CH:7][CH:6]=[CH:5][C:4]=3[C:3]=2[C:12]([O:14][CH3:15])=[O:13])[N:37]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 19077292Methyl 6-hydroxyquinoline-5-carboxylateHCID 190772944,6-Dimethoxy-2-methylsulfonylpyridine

Product 1

HCID 19962792Methyl 6-[(4,6-Dimethoxypyrimidin-2-yl)oxy]quinolin-5-carboxylateYield 89%

Procedure

0.8 g of methyl 6-hydroxyquinolin-5-carboxylate, 0.96 g of 4,6-dimethoxy-2-methylsulfonylpyridine and 0.82 g of potassium carbonate were stirred in 30 ml of N,N-dimethylformamide at 80° C. for 3 hours. The mixture was returned to room temperature, then poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from a solvent mixture of dichloromethane/isopropyl ether to obtain 1.21 g (yield: 89.0%) of the desired compound. mp: 160°-162° C.

Workup

  1. customwas returned to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe residue obtained by concentration under reduced pressure
  6. customwas crystallized from a solvent mixture of dichloromethane/isopropyl ether

Sources & evidence

ORD record
ord-e43d90e1663e4fddb1a11532e7b30547
Source dataset
uspto-grants-1997_04
Patent number
US05616537

Linked notes

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