Aluminium lithium hydride → 7-methyl-3-phenyl-2,3-dihydro-4H-1,4-benzoxazin-4-amine

HRID 2415820Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2415820
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:25]=[CH:24][C:11]2[N:12]([N:22]=O)[CH:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:14][O:15][C:10]=2[CH:9]=1>C(OCC)C.C1COCC1.CCCCCC>[CH3:7][C:8]1[CH:25]=[CH:24][C:11]2[N:12]([NH2:22])[CH:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:14][O:15][C:10]=2[CH:9]=1

Komponenten

6

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 223363397-methyl4-nitroso-3-phenyl-3,4-dihydro-2H-1,4-benzoxazine

Produkt 1

HCID 223363427-methyl-3-phenyl-2,3-dihydro-4H-1,4-benzoxazin-4-amineAusbeute 75,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A slurry of lithium aluminum hydride (6.9 g, 183 mmol) in ethyl ether (300 mL) is stirred in an ice bath under an argon atmosphere. A solution of 7-methyl-4-nitroso-3-phenyl-3,4-dihydro-2H-1,4-benzoxazine (23.22 g, 91.3 mmol) in ethyl ether (250 mL) and dry THF (40 mL) is added dropwise over 1.5 h. The mixture is removed from the ice bath and allowed to stir for 18 h. Water (50 mL) is slowly added, forming solids. The solids are collected by filtration and washed with ethyl ether. The resulting filtrates are combined and washed three times with water (400 mL), dried over magnesium sulfate, and concentrated to dryness to give a solid. The solids are slurried in hexane, collected, and dried to give 16.5 g (69%) of 7-methyl-3-phenyl-2,3-dihydro-4H-1,4-benzoxazin-4-amine.

Aufarbeitung

  1. customThe mixture is removed from the ice bath
  2. additionWater (50 mL) is slowly added
  3. customforming solids
  4. filtrationThe solids are collected by filtration
  5. washwashed with ethyl ether
  6. washwashed three times with water (400 mL)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated to dryness
  9. customto give a solid
  10. customcollected
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-80a4ac9b6d774dfd9f4284e41a636694
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06821970B2

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