Hydrochloric Acid → 2-(pyridin-3-yl)-4-(2-chloro-4-fluorophenyl)-4,6,7,8-tetrahydroquinazolin-5(1H)-one

HRID 1929538

Reaktionsgleichung

Reaktionsgleichung von HRID 1929538
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([NH2:10])=[NH:9])[CH:3]=1.[Cl:11][C:12]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:13]=1[CH:14]=O.[C:21]1(=O)[CH2:26][CH2:25][CH2:24][C:23](=[O:27])[CH2:22]1.C([O-])(=O)C.[Na+].Cl>C(O)C.O.C(OCC)(=O)C>[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[NH:10][C:21]3[CH2:26][CH2:25][CH2:24][C:23](=[O:27])[C:22]=3[CH:14]([C:13]3[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:12]=3[Cl:11])[N:9]=2)[CH:3]=1

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 104341,3-CyclohexanedioneHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 202042Nicotinamidine hydrochlorideHCID 517045Sodium Acetate

Produkt 1

HCID 250302972-(pyridin-3-yl)-4-(2-chloro-4-fluorophenyl)-4,6,7,8-tetrahydroquinazolin-5(1H)-oneAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3-pyridinecarboxamidine hydrochloride (Schaefer F. C., Peters G. A., et al. J. Org. Chem.; 1961; 26(2); 412-418.) 2.164 mmol, 2-chloro-4-fluorobenzaldehyde 2.164 mmol, 1,3-cyclohexanedione 2.164 mmol and sodium acetate 3.2 mmol were reacted in 8 ml of anhydrous ethanol under reflexing for 18 hr, condensed, to which ethyl acetate, water and 1N HCl were added and then the layers were separated. The water layer was adjusted with concentrated NaOH solution until the pH to be basic, then ethyl acetate was added and extracted twice. The organic layers were combined, dried over anhydrous sodium sulfate and separated by column chromatography to obtain a yellow solid of 0.21 g (yield 27%); 1H-NMR (400 MHz, CDCl3) δ 2.13-2.17 (2H, m, CH2); 2.43-2.51 (2H, m, CH2); 2.63-2.83 (2H, m, CH2); 6.06 (1H, s, CH); 7.15-7.22 (2H, m, ArH); 7.34-7.38 (1H, m, ArH); 8.07-8.09 (1H, m, ArH); 8.70-8.71 (1H, m, ArH); 8.89 (1H, m, ArH). MS (HREI) 355.0887 (M+).

Aufarbeitung

  1. customcondensed
  2. customthe layers were separated
  3. additionethyl acetate was added
  4. extractionextracted twice
  5. dry with materialdried over anhydrous sodium sulfate
  6. customseparated by column chromatography
  7. customto obtain a yellow solid of 0.21 g (yield 27%)

Quellen und Nachweise

ORD-Eintrag
ord-c7f175dbfd0c43549c510f6913488306
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188091B2

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