Hydrochloric Acid → 6-Methoxy-isoquinoline 2-oxide hydrochloride

HRID 1366737

Reaktionsgleichung

Reaktionsgleichung von HRID 1366737
[Cl:1]C1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[N:19][CH:18]=[CH:17]2.CO.Cl>ClCCl.C(OCC)C>[ClH:1].[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[N+:19]([O-:9])[CH:18]=[CH:17]2

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 70297m-Chloroperbenzoic acidHCID 110409786-Methoxyisoquinoline

Produkt 1

HCID 223973326-Methoxy-isoquinoline 2-oxide hydrochlorideAusbeute 80,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

At ambient temperature 133 g of m-chloroperbenzoic acid (purity 75%) was added in portions to a stirred solution of 6-methoxy-isoquinoline [Hendricks, J. B. and Rodriguez, C., J. Org. Chem. 1983, 48, 3344-3346; 79.8 g; 500 mmol] in 1.2 L of dichloromethane. Stirring was continued for 3 hours and subsequently methanol (1 L) was added. The bulk was reduced to 700 ml after which 800 ml of a saturated solution of hydrogen chloride in diethyl ether was added. Dilution with 1.5 L of diethyl ether resulted in precipitation of yellow crystals, which were separated by filtration, washed with chilled diethyl ether and dried in vacuo to give 6-methoxy-isoquinoline-N-oxide hydrochloride (85 g, 80%), (+)-FAB-MS 176 [M+H-HCl]+.

Aufarbeitung

  1. additionwas added
  2. customwere separated by filtration
  3. washwashed with chilled diethyl ether
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-25b9adb72939435998a8e21c12900c53
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893088B2

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