Ammonium Hydroxide → 2-(4,6-Difluoroindan-1-ylidene)-acetamide, (E)-

HRID 362822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 362822
[OH-].[NH4+:2].[F:3][C:4]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7]/[C:8]/2=[CH:14]\[C:15](Cl)=[O:16]>ClCCl>[F:3][C:4]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7]/[C:8]/2=[CH:14]\[C:15]([NH2:2])=[O:16]

Komponenten

4

Edukt 2

HCID 14923Ammonium HydroxideHCID 10977254(E)-2-(4,6-difluoro-1-indanylidene)acetyl Chloride

Produkt 1

HCID 101766722-(4,6-Difluoroindan-1-ylidene)-acetamide, (E)-Ausbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A 30% aqueous ammonium hydroxide solution (1.7 mL, 0.026 mol) was added dropwise to a stirred, chilled (ice bath) solution of (E)-2-(4,6-difluoro-1-indanylidene)acetyl chloride (2.97 g, 0.013 mol) in dichloromethane (50 mL). After 4.5 h the mixture was concentrated in vacuo and the residue was partitioned between 5% aqueous sodium bicarbonate solution and ethyl acetate. The ethyl acetate solution was washed with saturated aqueous sodium chloride, dried over sodium sulfate, filtered and concentrated in vacuo Chromatography on silica gel with ethyl acetate: hexanes (7:3)as eluent and trituration of the resulting solid with pentane gave 1.63 g (60%) of (E)-2-(4,6difluoro-1-indanylidene)acetamide as a white solid: mp 178°-180° C.; NMR (DMSO-d6): d 6.94-7.45 (m, 4H), 6.46 (s, 1H), 2.94-3.00, 3.21-3.27 (2 m's, 4H); steady-state nOe: irradiation at 6.46 d, observed 19% nOe at 7.26 d.

Aufarbeitung

  1. concentrationAfter 4.5 h the mixture was concentrated in vacuo
  2. customthe residue was partitioned between 5% aqueous sodium bicarbonate solution and ethyl acetate
  3. washThe ethyl acetate solution was washed with saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo Chromatography on silica gel with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b89f4fbba1b14f119cc7dfb0714fa327
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05872118

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