Dimethylformamide → 1-Cyano-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester

HRID 409189

Reaktionsgleichung

Reaktionsgleichung von HRID 409189
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10](Br)[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].[C:20]([Cu])#[N:21].CN(C)C=O.C(OCC)(=O)C>O>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([C:20]#[N:21])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 860145411-Bromo-4-hydroxy-isoquinoline-3-carboxylic acid butyl esterHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 671101221-Cyano-4-hydroxy-isoquinoline-3-carboxylic acid butyl esterAusbeute 46,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 1-bromo-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester (1.621 g, 5 mmol; prepared as shown in Scheme 2, according to US 2004/0254215 A1; 1H NMR (200 MHz, CD3OD) δ 11.89 (s, 1H), 8.41 (m, 1H), 8.25 (m, 1H), 7.84 (m, 2H), 4.49 (t, J=7.0 Hz, 2H), 1.87 (m, 2H), 1.47 (m, 2H), 1.00 (t, J=7.2 Hz, 3H)), CuCN (905 mg, 10 mmol) and dimethylformamide (20 mL) was refluxed with stirring under nitrogen for 5 min. After cooling to ambient temperature the mixture was diluted with water (300 mL). Then ethyl acetate (150 mL) was added and the mixture was shaken thoroughly for 5 min before it was filtered through a pad of celite. The organic phase of the filtrate was separated, and dried over MgSO4 before silica gel was added. The mixture was concentrated in vacuo. The residue was added on top of a short column filled with silica gel. Elution with dichloromethane gave the title compound as a yellowish solid (627 mg); MS-(−)-ion: M−1=269.2.

Aufarbeitung

  1. temperaturewas refluxed
  2. stirringthe mixture was shaken thoroughly for 5 min before it
  3. filtrationwas filtered through a pad of celite
  4. customThe organic phase of the filtrate was separated
  5. dry with materialdried over MgSO4 before silica gel
  6. additionwas added
  7. concentrationThe mixture was concentrated in vacuo
  8. additionThe residue was added on top of a short column
  9. additionfilled with silica gel
  10. washElution with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-3b2a248689cb4a558f5db224d09fb033
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759373B2

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