Potassium Hydroxide → 4-Benzyloxy-1-methoxymethyl-isoquinoline-3-carboxylic acid

HRID 1406213Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1406213
C([O:8][C:9]([C:11]1[N:12]=[C:13]([CH2:29][O:30][CH3:31])[C:14]2[C:19]([C:20]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:10])C1C=CC=CC=1.[OH-].[K+]>CCO>[CH2:22]([O:21][C:20]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH2:29][O:30][CH3:31])=[N:12][C:11]=1[C:9]([OH:10])=[O:8])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 667131694-Benzyloxy-1-methoxymethyl-isoquinoline-3-carboxylic acid benzyl ester

Produkt 1

HCID 667128924-Benzyloxy-1-methoxymethyl-isoquinoline-3-carboxylic acidAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 4-Benzyloxy-1-methoxymethyl-isoquinoline-3-carboxylic acid benzyl ester (198 mg, 0.48 mmol), KOH (325 mg, 5 mmol) and EtOH (10 ml) was stirred at ambient temperature for 18 h before the solvent was evaporated in vacuo. To the residue was added water (25 ml) and the mixture was washed with Et2O (2×25 ml). Then the solution was acidified by addition of aqueous 6N HCl and extracted with EtOAc (25 ml). The organic phase was dried over MgSO4 and concentrated in vacuo to give the title compound as a yellow oil (140 mg); MS-(+)-ion: M+1=324.1.

Aufarbeitung

  1. customwas evaporated in vacuo
  2. additionTo the residue was added water (25 ml)
  3. washthe mixture was washed with Et2O (2×25 ml)
  4. additionThen the solution was acidified by addition of aqueous 6N HCl
  5. extractionextracted with EtOAc (25 ml)
  6. dry with materialThe organic phase was dried over MgSO4
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8232264dc4cf4bbe84fc4d4ee3575bec
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08916585B2

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