Phosphorus oxychloride → 1H-Indole-3-carboxaldehyde, 1-methyl-2-phenyl-

HRID 436233

Reaktionsgleichung

Reaktionsgleichung von HRID 436233
P(Cl)(Cl)(Cl)=O.[CH3:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:22]([O-])(=[O:24])C.[Na+]>CN(C)C=O.O>[CH3:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH:22]=[O:24])=[C:8]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

6

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 770951-Methyl-2-phenylindoleHCID 517045Sodium Acetate

Produkt 1

HCID 744681H-Indole-3-carboxaldehyde, 1-methyl-2-phenyl-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To 150 ml of dimethylformamide 46 ml of phosphorus oxychloride were added dropwise care being taken that the temperature of the reaction mixture did not rise above 20° C. Subsequently to the obtained mixture 103.5 g of 1-methyl-2-phenyl-indole dissolved in 200 ml of dimethylformamide were added dropwise. During the addition the temperature of the reaction mixture was kept in the range of 20° to 40° C and thereupon for 1 hour between 40° and 45° C. Then the reaction mixture was poured into a solution of 490 g of sodium acetate dissolved in 500 ml of water to which 500 g of ice were added. The precipitated aldehyde was separated by suction, washed with water and methanol.

Aufarbeitung

  1. customdid not rise above 20° C
  2. additionwere added dropwise
  3. additionDuring the addition the temperature of the reaction mixture
  4. customwas kept in the range of 20° to 40° C
  5. additionwere added
  6. customThe precipitated aldehyde was separated by suction
  7. washwashed with water and methanol

Quellen und Nachweise

ORD-Eintrag
ord-95283ecf5330478b97733e8a59277787
Quelldatensatz
uspto-grants-1977_02
Patentnummer
US04008085

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