2-Methyl-2-butene → 3-(3-Methylisoxazol-5-yl)-2-oxo-4-phenyl-1,2-dihydroquinoline-6-carboxylic acid

HRID 2053429

Reaktionsgleichung

Reaktionsgleichung von HRID 2053429
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[C:8](=[O:25])[NH:9][C:10]3[C:15]([C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:14][C:13]([CH:23]=[O:24])=[CH:12][CH:11]=3)[O:4][N:3]=1.[OH:26]P([O-])(O)=O.[Na+].CC(=CC)C.Cl([O-])=O.[Na+]>C(O)(C)(C)C>[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[C:8](=[O:25])[NH:9][C:10]3[C:15]([C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:14][C:13]([C:23]([OH:26])=[O:24])=[CH:12][CH:11]=3)[O:4][N:3]=1

Komponenten

6

Edukt 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 1360186723-(3-Methyl-isoxazol-5-yl)-2-oxo-4-phenyl-1,2-dihydroquinoline-6-carboxaldehyde

Produkt 1

HCID 1354970603-(3-Methylisoxazol-5-yl)-2-oxo-4-phenyl-1,2-dihydroquinoline-6-carboxylic acidAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

3-(3-methyl-isoxazol-5-yl)-2-oxo-4-phenyl-1,2-dihydro-quinoline-6-carboxaldehyde (a) (16 mg, 0.05 mmol) was dissolved in tert-butanol (2 mL) followed by the sequential addition of saturated aqueous sodium phosphate monobasic solution (0.25 mL), 2-methyl-2-butene (0.05 mL), and sodium chlorite (NaClO2) (7 mg, 0.08 mmol). The mixture was stirred at room temperature for 3.5 h and concentrated. The residue was dissolved in ethyl acetate (15 mL), dried (MgSO4), filtered, and concentrated to give 3-(3-methylisoxazol-5-yl)-2-oxo-4-phenyl-1,2-dihydroquinoline-6-carboxylic acid (b) as a white solid (17.3 mg, 100%). 1H NMR (300 MHz, CD3OD) δ 8.19 (dd, J=6.4, 8.0 Hz, 1H), 7.96 (d, J=6.4 Hz, 1H), 7.51-7.43 (m, 4H), 7.31-7.23 (m, 2H), 6.33 (s, 1H), 2.18 (s, 3H). MS: 347.2 (M+H).

Aufarbeitung

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in ethyl acetate (15 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c13f8b6b22414c51b1939fd1420ada21
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07326788B2

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