Cesium carbonate → 6-(2,2-Dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline

HRID 257053

Reaktionsgleichung

Reaktionsgleichung von HRID 257053
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH2:6][CH2:5]2.[CH3:13][O:14][CH:15]([O:18][CH3:19])[CH2:16]Br.C([O-])([O-])=O.[Cs+].[Cs+].[I-].[Cs+]>CN(C=O)C>[CH3:13][O:14][CH:15]([O:18][CH3:19])[CH2:16][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH2:6][CH2:5]2

Komponenten

6

Edukt 4

HCID 10796Cesium carbonateHCID 24601Cesium iodideHCID 816722-Bromo-1,1-dimethoxyethaneHCID 159083146-Hydroxy-1,2,3,4-tetrahydroisoquinolin-1-one

Produkt 1

HCID 189638836-(2,2-Dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6-Hydroxy-1-oxo-1,2,3,4-tetrahydroisoquinoline is treated with bromacetaldehyde dimethyl acetal, in the presence of Cs2CO3 and CsI in DMF to yield 6-(2,2-dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline. Treatment with 2-chloromethylpyridine hydrochloride in the presence of sodium hydride in DMF yields 6-(2,2-dimethoxyethoxy)2-(2-pyridylmethyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline. Hydrolysis with 20% aqueous sulfuric acid in THF yields α-[2-(2-pyridylmethyl)-1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yloxy]-acetaldehyde which is then converted to 2-(2-pyridylmethyl)-6-[2-(N-hydroxyamino)-ethoxy]-1-oxo-1,2,3,4-tetrahydroisoquinoline.

Quellen und Nachweise

ORD-Eintrag
ord-ebf4cc4857a445ca810ceabd00a34116
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05260316

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