Acetic Anhydride → 6,7-Dimethoxy-1-methylisoquinolin-3-yl acetate

HRID 1620240Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1620240
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]([CH3:15])=[N:8][C:7]([OH:16])=[CH:6]2.CCN(C(C)C)C(C)C.[C:26](OC(=O)C)(=[O:28])[CH3:27]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:26]([O:16][C:7]1[N:8]=[C:9]([CH3:15])[C:10]2[C:5]([CH:6]=1)=[CH:4][C:3]([O:2][CH3:1])=[C:12]([O:13][CH3:14])[CH:11]=2)(=[O:28])[CH3:27]

Komponenten

6

Edukt 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 178486704HCID 178486704, Verbindung2×

Produkt 1

HCID 681821876,7-Dimethoxy-1-methylisoquinolin-3-yl acetateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 6,7-dimethoxy-1-methylisoquinolin-3-ol CCH 18060 (3.11 g, 14.19 mmol) in dry CH2Cl2 (230 mL) in a 500 mL round-bottomed flask equipped with a magnetic stirrer was added DIEA (2.46 mL, 14.88 mmol), DMAP (173 mg, 1.42 mmol) and acetic anhydride (1.39 mL, 14.80 mmol) and the reaction mixture was stirred overnight at RT. The organic solution was then washed with brine (50 mL), dried over Na2SO4, filtered and concentrated under vacuum. The residue was finally purified by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 50:50) to give 6,7-dimethoxy-1-methylisoquinolin-3-yl acetate SIL 32158 as an off-white solid (3.26 g, 88% yield).

Aufarbeitung

  1. washThe organic solution was then washed with brine (50 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe residue was finally purified by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 50:50)

Quellen und Nachweise

ORD-Eintrag
ord-b1b00fb04df7476a87295e2c00d0ebfe
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772316B2

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