Sodium periodate → 3-(2-Chloro-phenyl)-3,4-dihydro-quinazolin-4-one-2-carboxaldehyde

HRID 897046

Reaktionsgleichung

Reaktionsgleichung von HRID 897046
I([O-])(=O)(=O)=O.[Na+].[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]1[CH:25]=CN(C)C.N1C2C(=CC=CC=2)C(=[O:40])NC=1>O.O1CCCC1>[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]1[CH:25]=[O:40]

Komponenten

6

Edukt 3

HCID 23667635Sodium periodateHCID 536897693-(2-Chloro-phenyl)-2-(2-dimethylamino-vinyl)-3,4-dihydro-quinazolin-4-oneHCID 1354087534(1H)-Quinazolinone

Produkt 1

HCID 223474233-(2-Chloro-phenyl)-3,4-dihydro-quinazolin-4-one-2-carboxaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a well stirred mixture of sodium periodate (1.38 g, 6.45 mmol) in water (6 mL) and tetrahydrofuran (6 mL) was added 3-(2-chloro-phenyl)-2-(2-dimethylamino-vinyl)-3,4-dihydro-quinazolin-4-one (0.70 g, 2.15 mmol) all at once. The mixture warmed slightly to the touch and was stirred for 1 hour at ambient temperature. The reaction was filtered through celite and the pad was rinsed with ether. The filtrate was rendered basic by addition of saturated aqueous sodium bicarbonate and phases were separated. The aqueous layer was extracted with ethyl acetate. The combined organic phase was washed with brine, dried over potassium carbonate, and concentrated. The residue was flash chromatographed on silica gel (1×3 inches) with elution proceeding as follows: 50% methylene chloride/hexane (400 mL), nil; (100 mL) and 50% ethyl acetate/hexane (150 mL), 0.51 g (82%) of 3-(2-chloro-phenyl)-3,4-dihydro-quinazolin-4-one-2-carboxaldehyde as about a 1:1 mixture of free aldehyde and hydrate which contained about 20% of 3-(2-chloro-phenyl)-3,4-dihydro-quinazolin-4-one-2-carboxaldehyde (from simple hydrolysis of the enamine; exists exclusively in its enolized form to take advantage of an internal hydrogen bond to N1 of the quinazolin-4-one). Identifying features of each of the components of this mixture can be observed in the NMR spectrum as defined in the table below:

Aufarbeitung

  1. temperatureThe mixture warmed slightly to the touch
  2. stirringwas stirred for 1 hour at ambient temperature
  3. filtrationThe reaction was filtered through celite
  4. washthe pad was rinsed with ether
  5. additionThe filtrate was rendered basic by addition of saturated aqueous sodium bicarbonate and phases
  6. customwere separated
  7. extractionThe aqueous layer was extracted with ethyl acetate
  8. washThe combined organic phase was washed with brine
  9. dry with materialdried over potassium carbonate
  10. concentrationconcentrated
  11. customchromatographed on silica gel (1×3 inches) with elution proceeding
  12. addition(100 mL) and 50% ethyl acetate/hexane (150 mL), 0.51 g (82%) of 3-(2-chloro-phenyl)-3,4-dihydro-quinazolin-4-one-2-carboxaldehyde as about a 1:1 mixture of free aldehyde and hydrate which
  13. customfrom simple hydrolysis of the enamine

Quellen und Nachweise

ORD-Eintrag
ord-b4fafd426e324ee484a2520939a8b327
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06921764B2

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