Water → (9H-Pyrido[3,4-b]indol-1-yl)methanol

HRID 1733223Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1733223
[C:1]([C:5]1[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH:8]=[CH:7][N:6]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3)(OC)=[O:2].[H-].C([Al+]CC(C)C)C(C)C.O>O1CCCC1>[OH:2][CH2:1][C:5]1[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH:8]=[CH:7][N:6]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3

Komponenten

5

Edukt 3

HCID 962WaterHCID 597266Methyl 9H-pyrido(3,4-b)indole-1-carboxylateHCID 21225700Diisobutylaluminumhydride

Produkt 1

HCID 5318284(9H-Pyrido[3,4-b]indol-1-yl)methanolAusbeute 21,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In 50 ml of dry tetrahydrofuran were dissolved 160 mg of 1-carbomethoxy-9H-pyrido[3,4-b]indole. The solution was cooled with ice, 2 ml of diisobutyl-aluminum hydride were added and the reaction mixture allowed to stand for 2 hours. Unreacted reagent was then decomposed with a small amount of water and the mixture extracted with chloroform. The chloroform was removed by distillation and the residue recrystallized from methanol to yield 30 mg of 1-hydroxymethyl-9H-pyrido[3,4-b]indole as pale-yellow needles melting at 228°-230° C. The IR spectrum shows the absorption peak at 1680 cm-1 has disappeared, with an intense absorption being observed at 1630 cm-1. Mol. wt. (based on mass spectrum) 198.

Aufarbeitung

  1. additionwere added
  2. extractionthe mixture extracted with chloroform
  3. customThe chloroform was removed by distillation
  4. customthe residue recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-7cffc5dff0dd416793c130eddbf9adfa
Quelldatensatz
uspto-grants-1980_12
Patentnummer
US04241064

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