Iodine → 8-Hydroxy-2,2,4-trimethyl-1,2-dihydro-6-oxa-1-azachrysen-5-one

HRID 1043672Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1043672
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=3)[O:8][C:7](=[O:16])[C:6]=2[CH:17]=1.II>CC(C)=O.CN1CCCC1=O>[OH:15][C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[C:5]1[C:6](=[C:17]3[C:2](=[CH:3][CH:4]=1)[NH:1][C:5]([CH3:14])([CH3:6])[CH:4]=[C:3]3[CH3:2])[C:7](=[O:16])[O:8]2

Komponenten

5

Edukt 2

HCID 807IodineHCID 579905888-Amino-3-hydroxybenzo[c]chromen-6-one

Produkt 1

HCID 579906118-Hydroxy-2,2,4-trimethyl-1,2-dihydro-6-oxa-1-azachrysen-5-oneAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

In a pressure tube, 8-amino-3-hydroxybenzo[c]chromen-6-one (Reference Compound No. 1-(3), 40.0 g, 176 mmol) was dissolved in acetone (440 mL)-N-methylpyrrolidone (240 mL), iodine (17.9 g, 70.5 mmol) was added thereto, the pressure tube was sealed, and then the reaction mixture was stirred at 110° C. for 3 days. After cooling down, acetone was removed under reduced pressure. To the obtained residue, ethyl acetate (700 mL), hexane (150 mL) and 1% aqueous sodium thiosulfate solution (700 mL) were added thereto and the mixture was separated into a water phase and an organic layer. The water layer was extracted with a mixed solvent of ethyl acetate (250 mL)-hexane (50 mL) (3 times). The combined organic layer was washed with water (500 mL, 3 times) and saturated brine (500 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. To the obtained residue, chloroform (150 mL) was added and the unsoluble materials were filtered out. After the filtrate was concentrated, the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (26.0 g) as a yellow solid. (Yield 48%)

Aufarbeitung

  1. additionwas added
  2. customthe pressure tube was sealed
  3. temperatureAfter cooling down
  4. customacetone was removed under reduced pressure
  5. additionTo the obtained residue, ethyl acetate (700 mL), hexane (150 mL) and 1% aqueous sodium thiosulfate solution (700 mL) were added
  6. customthe mixture was separated into a water phase
  7. extractionThe water layer was extracted with a mixed solvent of ethyl acetate (250 mL)-hexane (50 mL) (3 times)
  8. washThe combined organic layer was washed with water (500 mL, 3 times) and saturated brine (500 mL) successively
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was removed under reduced pressure
  11. additionTo the obtained residue, chloroform (150 mL) was added
  12. filtrationthe unsoluble materials were filtered out
  13. concentrationAfter the filtrate was concentrated
  14. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-cd2b8ef7abaa4c7b9eed8816e0723690
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563551B2

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