Hydrochloric Acid → 5-methyl-5H-pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine

HRID 2072696Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2072696
Cl.[CH3:2][N:3]([N:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH:18]=O)[C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[N+:10]([O-])=O.[OH-].[Na+]>O1CCCC1>[CH3:2][N:3]1[C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=[CH:18][C:14]2=[CH:15][CH:16]=[CH:17][N:13]12

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 142321061-[N-methyl-N-(3-nitro-4-pyridinyl)amino]pyrrole-2-carboxaldehyde2×

Produkt 1

HCID 146019475-methyl-5H-pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepineAusbeute 44,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To cold, concentrated hydrochloric acid (200 ml) was added, in the following order, 100 g of stannous chloride dihydrate, 200 ml of tetrahydrofuran, and a solution of 28 g of 1-[N-methyl-N-(3-nitro-4-pyridinyl)amino]pyrrole-2-carboxaldehyde in 150 ml of tetrahydrofuran. Upon completion of the 1-[N-methyl-N-(3-nitro-4-pyridinyl)amino]pyrrole-2-carboxaldehyde addition, the reaction was poured into an aqueous solution of sodium hydroxide (200 g in 1 liter of water), stirred for five minutes, and then extracted with ethyl acetate. The organic layer was washed with water followed by a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated. The resultant oil was purified by means of high pressure liquid chromatography (silica gel; elution with ethyl acetate) to afford 10 g (38%) of 5-methyl-5H-pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine as an oil, IR(CHCl3) C=N @ 1610 cm-1 ; MS(EI)M+ @ 199 (100%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resultant oil was purified by means of high pressure liquid chromatography (silica gel; elution with ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-26644271ef1a4099ac4173c51ea0652e
Quelldatensatz
uspto-grants-1990_04
Patentnummer
US04914103

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