Dimethylformamide → 1-Chloro-3-methyl-isoquinoline-4-carbaldehyde

HRID 606303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 606303
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([Cl:12])=[N:4][C:3]=1[CH3:13].CN([CH:17]=[O:18])C>CCCCCC.C1COCC1>[Cl:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([CH:17]=[O:18])=[C:3]([CH3:13])[N:4]=1

Komponenten

5

Edukt 2

HCID 6228DimethylformamideHCID 825722444-Bromo-1-chloro-3-methyl-isoquinoline

Produkt 1

HCID 866159291-Chloro-3-methyl-isoquinoline-4-carbaldehydeAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

n-BiLi (12.3 ml of 1.6 M in hexane, 20 mmol) is added dropwise to a solution of 4-bromo-1-chloro-3-methyl-isoquinoline (4.6 g, 18 mmol) in THF (80 ml) at −78° C. and the mixture is stirred for 40 min. DMF (4.2 ml, 54 mmol) is then added slowly. The cold bath is removed, and stirring is continued for 15 min. The mixture is acidified with 1N—HCl to pH 2 and extracted with ether. The combined extracts are dried over Na2SO4 and concentrated in vacuo. The residue is chromatographed on silica gel to give 3.0 g of 1-chloro-3-methyl-isoquinoline-4-carbaldehyde. 1H NMR (CDCl3) 10.9 (s, 1H), 9.06 (d, 1H), 8.40 (d, 1H), 7.88 (t, 1H), 7.70 (t, 1H), 2.99 (s, 3H).

Aufarbeitung

  1. customThe cold bath is removed
  2. stirringstirring
  3. waitis continued for 15 min
  4. extractionextracted with ether
  5. dry with materialThe combined extracts are dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue is chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f78d00767bec4bf2a2b72330d71cc318
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915288B2

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