Nitroethane → 6-chloro-5-fluoro-3-(2-nitro-propenyl)-1H-indole

HRID 1946555Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1946555
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=O)=[CH:7][NH:8]2)=[CH:4][C:3]=1[F:13].C([O-])(=O)C.[NH4+].[N+:19]([CH2:22][CH3:23])([O-:21])=[O:20]>>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[C:22]([N+:19]([O-:21])=[O:20])[CH3:23])=[CH:7][NH:8]2)=[CH:4][C:3]=1[F:13]

Komponenten

4

Edukt 3

HCID 6587NitroethaneHCID 517165Ammonium AcetateHCID 210715286-chloro-5-fluoro-1H-indole-3-carbaldehyde

Produkt 1

HCID 669644686-chloro-5-fluoro-3-(2-nitro-propenyl)-1H-indoleAusbeute 97 %

Versuchsvorschrift

The solution (0.2 M) of 6-chloro-5-fluoro-1H-indole-3-carbaldehyde (4.0 g, 20.24 mmol) in nitroethane (100 mL) was refluxed with ammonium acetate (1.32 g, 0.85 mmol) for 4 hours. The reaction mixture was concentrated under vacuum to remove nitroethane, diluted with ethylacetate and washed with brine. The organic layer was concentrated to give 6-chloro-5-fluoro-3-(2-nitro-propenyl)-1H-indole (5.0 g, 97%) as a reddish orange solid. 1H NMR (500 MHz, CDCl3): δ 8.77 (s, 1H), 8.32 (s, 1H), 7.58 (d, 1H, J=2.5 Hz), 7.54 (d, 1H, J=9 Hz), 7.50 (d, 1H, J=5.9 Hz), 2.52 (s, 3H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customto remove nitroethane
  3. additiondiluted with ethylacetate
  4. washwashed with brine
  5. concentrationThe organic layer was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-3f1f6a64946e4b12a6c2957e61b484cf
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399453B2

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