Thionyl Chloride → 1-Chloro-4-chloromethyl-3-methyl-isoquinoline

HRID 606304

Reaktionsgleichung

Reaktionsgleichung von HRID 606304
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH:18]=O)=[C:10]([CH3:20])[N:9]=1.O=S(Cl)[Cl:23]>C1COCC1.C(Cl)Cl>[Cl:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH2:18][Cl:23])=[C:10]([CH3:20])[N:9]=1

Komponenten

6

Edukt 3

HCID 24386Thionyl ChlorideHCID 21226445Aluminium lithium hydrideHCID 86615929HCID 86615929, Verbindung

Produkt 1

HCID 866159311-Chloro-4-chloromethyl-3-methyl-isoquinolineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

LAH (3.6 ml of 1M in THF, 3.62 mmol) is added to a solution of 1-chloro-3-methyl-isoquinoline-4-carbaldehyde (744 mg, 3.62 mmol) in THF (10 ml) at 0° C. After stirring for 30 min at ambient temperature, the mixture is quenched with small amounts of saturated sodium sulfate and filtered through a pad of celite. The filtrate is concentrated in vacuo to give the crude alcohol. SOCl2 (13 ml of 2M in DCM, 25 mmol) is added to a solution of the crude alcohol in DCM (5 ml). After stirring for 1 h at room temperature, the mixture is concentrated in vacuo and the residue is chromatographed on silica gel to give 737 mg of 1-chloro-4-chloromethyl-3-methyl-isoquinoline. 1H NMR (CDCl3) 8.44 (d, 1H), 8.18 (d, 1H), 8.02 (t, 1H), 7.82 (t, 1H), 5.03 (s, 2H), 3.00 (s, 3H).

Aufarbeitung

  1. customthe mixture is quenched with small amounts of saturated sodium sulfate
  2. filtrationfiltered through a pad of celite
  3. concentrationThe filtrate is concentrated in vacuo
  4. customto give the crude alcohol
  5. stirringAfter stirring for 1 h at room temperature
  6. concentrationthe mixture is concentrated in vacuo
  7. customthe residue is chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-5c0e840b92554b8ba569216e3d66857b
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915288B2

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