Reaktionsgleichung
[F:1][C:2]1[CH:21]=[C:20]([I:22])[CH:19]=[CH:18][C:3]=1[NH:4][C:5]1[C:6]([C:13]([O:15]CC)=[O:14])=[CH:7][N:8]([CH3:12])[C:9](=[O:11])[CH:10]=1.[OH-].[Na+]>CCO.Cl>[F:1][C:2]1[CH:21]=[C:20]([I:22])[CH:19]=[CH:18][C:3]=1[NH:4][C:5]1[C:6]([C:13]([OH:15])=[O:14])=[CH:7][N:8]([CH3:12])[C:9](=[O:11])[CH:10]=1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
Ethyl 4-(2-fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate (140 mg, 0.34 mmol) was suspended in EtOH (10 mL), to which was added 1 M NaOH (10 mL). This mixture was stirred at R.T. for 15 h., then diluted with 1 M HCl (50 mL) and the resulting precipitate extracted into EtOAc (2×50 mL). The combined EtOAc fractions were dried (Na2SO4) and the solvent removed under reduced pressure to afford 4-(2-fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid as a white solid (132 mg, 100%), m.p. (acetone/MeOH) 254-257° C. 1H NMR [(CD3)2SO, 400 MHz] δ 13.30 (v br s, 1H), 9.66 (s, 1H), 8.52 (s, 1H), 7.76 (dd, J=10.1, 1.9 Hz, 1H), 7.59 (ddd, J=8.4, 1.7, 0.8 Hz, 1H), 7.31 (t, J=8.5 Hz, 1H), 5.49 (d, J=0.7 Hz, 1H), 3.41 (s, 3H). Anal. Calcd for C13H10FIN2O3: C, 40.2; H, 2.6; N, 7.2. Found: C, 40.5; H, 2.3; N, 7.3.
Aufarbeitung
- extractionthe resulting precipitate extracted into EtOAc (2×50 mL)
- dry with materialThe combined EtOAc fractions were dried (Na2SO4)
- customthe solvent removed under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-b90a675c711645bfaf43e12e57157bc7
- Quelldatensatz
- uspto-grants-2007_09
- Patentnummer
- US07273877B2
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