Dimethylamine → 5-methyl-3-phenyl-6-(p-[dimethylaminomethyl]phenyl)-isoxazolo[4,5-c]pyridin-4(5H)-one

HRID 2083789

Reaktionsgleichung

Reaktionsgleichung von HRID 2083789
[CH3:1][N:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14]Br)=[CH:10][CH:9]=2)=[CH:6][C:5]2[O:16][N:17]=[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:4]=2[C:3]1=[O:25].[CH3:26][NH:27][CH3:28]>C1(C)C=CC=CC=1>[CH3:1][N:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][N:27]([CH3:28])[CH3:26])=[CH:10][CH:9]=2)=[CH:6][C:5]2[O:16][N:17]=[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:4]=2[C:3]1=[O:25]

Komponenten

4

Edukt 2

HCID 674DimethylamineHCID 220155615-Methyl-3-phenyl-6-(p-bromomethylphenyl)-isoxazolo[4,5-c]pyridin-4(5H)-one2×

Produkt 1

HCID 3345095-methyl-3-phenyl-6-(p-[dimethylaminomethyl]phenyl)-isoxazolo[4,5-c]pyridin-4(5H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 21.2 g. of the product of Example 4, containing 62% of 5-methyl-3-phenyl-6-(p-bromomethylphenyl)-isoxazolo[4,5-c]pyridin-4(5H)-one 0.0332 mole of bromo compound) and 7.2 g. (0.160 mole) dimethylamine in 300 ml. toluene is stirred overnight at room temperature. The mixture is filtered and the solid washed with toluene and the solvent evaporated in vacuo. The resulting solid is dissolved in methylene chloride and treated with 2N hydrochloric acid, the precipitate is then filtered, washed with water and ether. The solid is then dissolved in methylene chloride and 2N sodium dioxide and the organic phases separated and washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to give 5-methyl-3-phenyl-6-(p-[dimethylaminomethyl]phenyl)-isoxazolo[4,5-c]pyridin-4(5H)-one; m.p. 159°-161° C.

Aufarbeitung

  1. additionA mixture of 21.2 g
  2. filtrationThe mixture is filtered
  3. washthe solid washed with toluene
  4. customthe solvent evaporated in vacuo
  5. dissolutionThe resulting solid is dissolved in methylene chloride
  6. additiontreated with 2N hydrochloric acid
  7. filtrationthe precipitate is then filtered
  8. washwashed with water and ether
  9. dissolutionThe solid is then dissolved in methylene chloride
  10. custom2N sodium dioxide and the organic phases separated
  11. washwashed with water
  12. dry with materialdried over anhydrous magnesium sulfate
  13. filtrationfiltered
  14. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6a874e1980214817a9b05c8243a88056
Quelldatensatz
uspto-grants-1978_04
Patentnummer
US04086421

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