Methanol → Methyl 6-hydroxyisoquinoline-3-carboxylate

HRID 1640120Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1640120
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][NH:7][CH:6]([C:12]([OH:14])=[O:13])[CH2:5]2.S(Cl)(Cl)=O.[CH3:19]O>>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([C:12]([O:14][CH3:19])=[O:13])=[CH:5]2

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 27331741,2,3,4-Tetrahydro-6-hydroxy-3-isoquinolinecarboxylic acid

Produkt 1

HCID 135742191Methyl 6-hydroxyisoquinoline-3-carboxylateAusbeute 67 %

Versuchsvorschrift

To a solution of 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (1.0 g, 5.2 mmol) in MeOH (50 mL) was added thionyl chloride (0.56 mL, 7.8 mmol) slowly. The reaction was heated at reflux for 18 h and then cooled to rt. The solvent was evaporated. The residue was redissolved in DCM and saturated NaHCO3 solution was added. The mixture was extracted with DCM (2×) and the combined organic solutions were dried over Na2SO4 and concentrated to give methyl 6-hydroxyisoquinoline-3-carboxylate as a white solid (0.72 g, 67%). LCMS: (FA) ES+ 208.2.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 18 h
  3. customThe solvent was evaporated
  4. dissolutionThe residue was redissolved in DCM
  5. additionsaturated NaHCO3 solution was added
  6. extractionThe mixture was extracted with DCM (2×)
  7. dry with materialthe combined organic solutions were dried over Na2SO4
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-79744b2c1c2341928de9b8497fedc2db
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110687B2

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