Dimethylformamide → 2-chloro-1H-indole-3-carbaldehyde

HRID 18295

Reaktionsgleichung

Reaktionsgleichung von HRID 18295
P(Cl)(Cl)([Cl:3])=O.[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][C:7]1=O.CN([CH:19]=[O:20])C>>[Cl:3][C:7]1[NH:6][C:14]2[C:9]([C:8]=1[CH:19]=[O:20])=[CH:10][CH:11]=[CH:12][CH:13]=2

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 321710Oxindole

Produkt 1

HCID 3147912-chloro-1H-indole-3-carbaldehydeAusbeute 84 %

Versuchsvorschrift

To DMF (30 mL) with stirring at 0° C. was added dropwise phosphorus oxychloride (10 mL, 107 mmole) over 5 minutes. The reaction was stirred for an additional 15 minutes, then oxindole (6.0 g, 45 mmole) was added portionwise over 5 min. The reaction was allowed to warm to RT and stirred for 18 h then was carefully poured into ice water (350 mL). The solution was stirred for 6 h after which time a suspension formed. The solids were filtered off, washed with cold water, pressed dry and dried under vacuum to give the title compound (6.83 g, 84%) as a yellowish solid: 1H NMR (400 MHz, d6-DMSO) δ 10.0 (s, 1 H), 8.05 (dd, 1 H), 7.43 (dd, 1 H), 7.23-7.31 (m, 2 H); MS (ES) m/e 179.0 (M+H)+.

Aufarbeitung

  1. stirringstirred for 18 h
  2. stirringThe solution was stirred for 6 h after which time a suspension
  3. customformed
  4. filtrationThe solids were filtered off
  5. washwashed with cold water
  6. custompressed dry
  7. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ba0495c59be74b60a5e6e57cf5c55ba7
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741339B2

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