Dimethylformamide → 1-Methyl-2,5-dichloroindole-3-carbaldehyde

HRID 1735095Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1735095
O=P(Cl)(Cl)[Cl:3].[CH3:6][N:7]([CH:9]=O)[CH3:8].CN1C2[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=2)[CH2:14][C:13]1=[O:22].C([O-])(O)=O.[Na+]>ClCCl.N1C=CC=CC=1>[CH3:8][N:7]1[C:6]2[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=2)[C:14]([CH:13]=[O:22])=[C:9]1[Cl:3]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 109761125-chloro-1-methyl-2,3-dihydro-1H-indol-2-one

Produkt 1

HCID 190689371-Methyl-2,5-dichloroindole-3-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

POCl3 (6 ml) was added dropwise to a mixture of dry DMF (5.9 ml) and dichloromethane (5.9 ml) kept at 0° C. 1-Methyl-5-chloro-1,3-dihydroindol-2-one (4.0 g) dissolved in dichloromethane (20 ml) and pyridine (2.9 ml) was added dropwise at 0° C. over a period of 30 min. Subsequent stirring at room temperature for 3h. The mixture was poured onto icewater (500 ml) neutralized with NaHCO3 whereafter the mixture was stirred overnight. The precipitate was filtered off, washed with water and dried. The crude material (4.45 g) was recrystallized from ethanol yielding 1.27 g (25.4%) of (45). M.p. 165°-167° C.

Aufarbeitung

  1. customkept at 0° C
  2. additionThe mixture was poured onto icewater (500 ml)
  3. stirringwas stirred overnight
  4. filtrationThe precipitate was filtered off
  5. washwashed with water
  6. customdried
  7. customThe crude material (4.45 g) was recrystallized from ethanol yielding 1.27 g (25.4%) of (45)

Quellen und Nachweise

ORD-Eintrag
ord-983dc1edfaa94b39ad284fa1a3bf8d99
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05536721

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