Acetic Anhydride → HCID 68613661, Verbindung

HRID 1993102Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1993102
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[C:7]2[CH3:12].[C:13](OC(=O)C)(=[O:15])[CH3:14]>N1C=CC=CC=1>[C:13]([O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[C:7]2[CH3:12])(=[O:15])[CH3:14]

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 178306411-Methylisoquinolin-5-ol

Produkt 1

HCID 68613661HCID 68613661, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

For example, 5-hydroxy-1-methylisoquinoline 64.9, prepared as described in J. Med. Chem., 1968, 11, 700, is reacted with acetic anhydride in pyridine to afford 5-acetoxy-1-methylisoquinoline 64.10. The latter compound is reacted with N-bromosuccinimide in refluxing ethyl acetate to yield 5-acetoxy-1-bromomethylisoquinoline 64.11. The product is then reacted with five molar equivalents of a trialkyl phosphite at 120° to give the phosphonate product 64.12. The acetoxy group is hydrolyzed by reaction with sodium bicarbonate in aqueous methanol as described in J. Am. Chem. Soc., 93, 746, 1971, to produce the phenol 64.13.

Quellen und Nachweise

ORD-Eintrag
ord-172d6d35377b4dc1987ff8d01f1fc96a
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07649015B2

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