Diphenyl Ether → 7-(3,5-Dimethylisoxazol-4-yl)-6-methoxyquinolin-4-ol

HRID 81977Notes

Reaction equation

HRID 81977 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11](=[O:20])[C:12](C(O)=O)=[CH:13][NH:14]3)=[CH:9][C:8]=2[O:21][CH3:22])=[C:5]([CH3:23])[O:4][N:3]=1.C1(OC2C=CC=CC=2)C=CC=CC=1>C(OCC)C>[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11](=[O:20])[CH:12]=[CH:13][NH:14]3)=[CH:9][C:8]=2[O:21][CH3:22])=[C:5]([CH3:23])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 574655867-(3,5-Dimethyl-4-isoxazolyl)-4-hydroxy-6-(methyloxy)-3-quinolinecarboxylic acid

Product 1

HCID 681878107-(3,5-Dimethylisoxazol-4-yl)-6-methoxyquinolin-4-olYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

7-(3,5-Dimethyl-4-isoxazolyl)-6-(methyloxy)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid (for a preparation see Intermediate 5) (8 g, 25.5 mmol) was added in small portions to refluxing diphenyl ether (150 ml) and the resulting solution was stirred for 30 min, then allowed to cool to 35° C. before addition of diethyl ether (200 ml). The resulting suspension was filtered and the solid product washed with ether (100 ml) to give 7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-4(1H)-quinolinone (6.9 g, 25.5 mmol, 100% yield) as a beige solid. LCMS (formate) Rt 0.61, MH+ 271.

Workup

  1. additionwas added in small portions
  2. filtrationThe resulting suspension was filtered
  3. washthe solid product washed with ether (100 ml)

Sources & evidence

ORD record
ord-8bc4331efea440b7bcd4650c456bfb68
Source dataset
uspto-grants-2014_09
Patent number
US08846709B2

Reaction notes

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