Thionyl Chloride → 7-Benzyloxy-4-hydroxy-isoquinoline-3-carboxylic acid ethyl ester

HRID 409328Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 409328
[CH2:1]([O:3][C:4]([C:6]1[N:7](CC2C=CC(OC)=CC=2OC)[CH2:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:10]=2)=[O:5])[CH3:2].S(Cl)(Cl)=O>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:10]=2)=[O:5])[CH3:2]

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 671104847-Benzyloxy-2-(2,4-dimethoxy-benzyl)-4-hydroxy-1,2-dihydro-isoquinoline-3-carboxylic acid ethyl ester

Produkt 1

HCID 671103537-Benzyloxy-4-hydroxy-isoquinoline-3-carboxylic acid ethyl esterAusbeute 69,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Dichloromethane (100 mL) was cooled to 0° C. and 5.7 g (12 mmol) of 7-benzyloxy-2-(2,4-dimethoxy-benzyl)-4-hydroxy-1,2-dihydro-isoquinoline-3-carboxylic acid ethyl ester and 1.31 mL (18 mmol) of thionyl chloride were added. The reaction was stirred for one hour and then allowed to warm to room temperature and stirred for an additional 3 hours. 60 mL of hexanes was added to the resultant slurry and the white solid was collected by filtration through a medium glass fitted filter. The solid was partitioned between ethyl acetate and saturated sodium bicarbonate solution and the organic phase was washed with brine, dried over anhydrous sodium sulfate, and concentrated to give the title compound (2.7 g, white solid); MS (ESI+): 324.3 e/z (M+1)

Aufarbeitung

  1. stirringstirred for an additional 3 hours
  2. filtrationthe white solid was collected by filtration through a medium glass
  3. customfitted
  4. filtrationfilter
  5. customThe solid was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  6. washthe organic phase was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5608c88c89f54e978f3461e9d5cd92b5
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759373B2

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