4-Chlorobenzoyl chloride → 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-carboxaldehyde

HRID 1195885

Reaktionsgleichung

Reaktionsgleichung von HRID 1195885
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[CH:13]=[O:14].[H-].[Na+].[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1.C(OCC)(=O)C>CN(C)C=O.O>[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([N:8]2[C:9]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[C:6]([CH:13]=[O:14])=[C:7]2[CH3:12])=[O:23])=[CH:20][CH:19]=1

Komponenten

7

Edukt 4

HCID 85014-Chlorobenzoyl chlorideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 31595805-Methoxy-2-methyl-1H-indole-3-carbaldehyde

Produkt 1

HCID 108927871-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-carboxaldehydeAusbeute 82,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
-60 °C

Versuchsvorschrift

To a solution of 5-methoxy-2-methyl-1H-indole-3-carboxaldehyde (20 g, 106 mmol) in 210 ml of dry dimethylformamide is added oil free sodium hydride (2.7 g, 111 mmol). The reaction mixture is stirred for five hours at which time it is cooled to -60° C., and freshly distilled 4-chlorobenzoyl chloride (14.4 ml, 117 mmol) is added dropwise. It is stirred for an additional 10 minutes and worked up by pouring the cold paste into cold ethyl acetate and water. The organic phase is washed once with dilute sodium bicarbonate solution, once again with water, and once with a saturated solution of sodium chloride. It is further dried with magnesium sulfate, filtered, and concentrated in vacuo to a solid which is stirred vigorously with 50 ml of methanol for two hours. The solid is filtered and dried to give 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-carboxaldehyde (28.7 g, 82.5%). A portion which is recrystallized from ethyl acetate has a mp of 150.5°-151.5° C.

Aufarbeitung

  1. stirringIt is stirred for an additional 10 minutes
  2. washThe organic phase is washed once with dilute sodium bicarbonate solution, once again with water
  3. dry with materialIt is further dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a solid which
  6. stirringis stirred vigorously with 50 ml of methanol for two hours
  7. filtrationThe solid is filtered
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2f2ef95cde954819b682cb23a636311b
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05112846

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