Sodium Bicarbonate → 3-(3-Methyl-isoxazol-5-yl)-2-oxo-4-phenyl-1,2-dihydroquinoline-6-carboxaldehyde

HRID 2053428

Reaction equation

HRID 2053428 reaction equation
[OH:1][CH:2]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[C:9]([C:16]1[O:20][N:19]=[C:18]([CH3:21])[CH:17]=1)=[C:8]2[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)CO.I([O-])(=O)(=O)=O.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:21][C:18]1[CH:17]=[C:16]([C:9]2[C:10](=[O:15])[NH:11][C:12]3[C:7]([C:8]=2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:6][C:5]([CH:2]=[O:1])=[CH:14][CH:13]=3)[O:20][N:19]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 23667635Sodium periodateHCID 1354945476-(1,2-dihydroxy-ethyl)-3-(3-methyl-isoxazol-5-yl)-4-phenyl-1H-quinolin-2-one

Product 1

HCID 1360186723-(3-Methyl-isoxazol-5-yl)-2-oxo-4-phenyl-1,2-dihydroquinoline-6-carboxaldehydeYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-(1,2-dihydroxy-ethyl)-3-(3-methyl-isoxazol-5-yl)-4-phenyl-1H-quinolin-2-one (40 mg, 0.11 mmol), sodium periodate (94 mg, 0.44 mmol), saturated aqueous sodium bicarbonate (0.2 mL), and DCM (5 mL) was stirred for 4 h at room temperature, then filtered and concentrated. The residue was purified by flash chromatography on silica gel to provide 3-(3-methyl-isoxazol-5-yl)-2-oxo-4-phenyl-1,2-dihydroquinoline-6-carboxaldehyde (a) as a white solid (31 mg, 85%).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-d600bb1a006c43588c1f18b8a05f1202
Source dataset
uspto-grants-2008_02
Patent number
US07326788B2

Linked notes

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