Dimethylformamide → 1-Chloro-6-methoxy-3-methyl-isoquinoline-4-carbaldehyde

HRID 606312

Reaktionsgleichung

Reaktionsgleichung von HRID 606312
[Li]CCCC.Br[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[C:10]([Cl:19])=[N:9][C:8]=1[CH3:20].CN([CH:24]=[O:25])C>C1COCC1>[Cl:19][C:10]1[C:11]2[C:16](=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[C:7]([CH:24]=[O:25])=[C:8]([CH3:20])[N:9]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 866159324-Bromo-1-chloro-6-methoxy-3-methylisoquinolineHCID 178418339Butyllithium

Produkt 1

HCID 866159331-Chloro-6-methoxy-3-methyl-isoquinoline-4-carbaldehydeAusbeute 72,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

n-BuLi (12 ml of 1.6 M in hexane) is added dropwise to a solution of 4-bromo-1-chloro-6-methoxy-3-methyl-isoquinoline (4.8 g, 17 mmol) in THF (60 ml) at −78° C. After stirring for 40 min, DMF (4 ml, 51 mmol) is added slowly. The reaction is allowed to warm to 0° C. and the stirring is continued for 1 h. The mixture is then quenched with 1N—HCl (30 ml) and extracted with EtOAc. The combined extracts are dried over Na2SO4 and evaporated. The residue is chromatographed on silica gel eluting with EtOAc/hexane (1:4) to give 2.9 g of 1-chloro-6-methoxy-3-methyl-isoquinoline-4-carbaldehyde. 1H NMR (CDCl3) 10.8 (s, 1H), 8.61 (s, 1H), 8.24 (d, 1H), 7.29 (d, 1H), 4.01 (s, 3H), 2.99 (s, 3H).

Aufarbeitung

  1. waitthe stirring is continued for 1 h
  2. customThe mixture is then quenched with 1N—HCl (30 ml)
  3. extractionextracted with EtOAc
  4. dry with materialThe combined extracts are dried over Na2SO4
  5. customevaporated
  6. customThe residue is chromatographed on silica gel eluting with EtOAc/hexane (1:4)

Quellen und Nachweise

ORD-Eintrag
ord-430a20bdee074d54a2da199c33df1690
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915288B2

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