Sodium Hydroxide → 2-(3-Benzo[b]furyl)-6,7-methylenedioxyquinolin-4-one

HRID 38647

Reaktionsgleichung

Reaktionsgleichung von HRID 38647
[C:1]([C:4]1[C:5]([NH:13][C:14]([C:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[O:18][CH:17]=2)=O)=[CH:6][C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1)(=[O:3])[CH3:2].[OH-].[Na+]>O1CCOCC1>[O:18]1[CH:17]=[C:16]([C:14]2[CH2:2][C:1](=[O:3])[C:4]3[C:5](=[CH:6][C:7]4[O:11][CH2:10][O:9][C:8]=4[CH:12]=3)[N:13]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]1=2

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 44220313N-(6-acetyl-1,3-benzodioxol-5-yl)-1-benzofuran-3-carboxamide

Produkt 1

HCID 666593752-(3-Benzo[b]furyl)-6,7-methylenedioxyquinolin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

The synthetic procedure of target compounds 158 is illustrated in Scheme 12. The starting 2-amino-4,5-methylenedioxy acetophenone (148) was first reacted with benzo[b]furan-3-carbonyl chloride (154) to give N-(6-Acetyl-1,3-benzodioxol-5-yl)-1-benzofuran-3-carboxamide (155). Then, the intermediates (155) was subjected to cyclization in dioxane, in the presence of NaOH, to afford 2-(3-Benzo[b]furyl)-6,7-methylenedioxyquinolin-4-one (156). Compound 156 was first reacted with tetrabenzylpyrophosphate in THF, in the presence of NaH, to yield dibenzyl 2-(3-benzo[b]furyl)-6,7-methylenedioxyquinolin-4-yl phosphate (157). Compound 157 was then subjected to catalytic hydrogenation in MeOH to give its diphosphoric acid (158).

Quellen und Nachweise

ORD-Eintrag
ord-ae9c7abb54ae4f0e8f12be6e368aed35
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524740B2

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