Potassium Carbonate → N-cyclopropyl-4,5-difluoro-2-nitroaniline

HRID 1048952Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1048952
F[C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[F-].[K+].C(=O)([O-])[O-].[K+].[K+].[CH:21]1([NH2:24])[CH2:23][CH2:22]1>ClCCl>[CH:21]1([NH:24][C:2]2[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=2[N+:10]([O-:12])=[O:11])[CH2:23][CH2:22]1

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 69828CyclopropylamineHCID 750121,2,4-Trifluoro-5-nitrobenzeneHCID 522689Potassium Fluoride

Produkt 1

HCID 86703086N-cyclopropyl-4,5-difluoro-2-nitroaniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

2,4,5-Trifluoronitrobenzene (2.00 g, 11.3 mmol), potassium fluoride (0.656 g, 11.3 mmol), potassium carbonate (1.561 g, 11.29 mmol), and cyclopropylamine (0.93 ml, 13.55 mmol) were added to a vial and heated in a microwave at 90° C. for 10 min. The reaction was then diluted with dichloromethane, washed with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure. Purification by flash chromatography on silica gel (0-15% ethyl acetate in hexanes) provided the title compound: 1H NMR (500 MHz, CDCl3) δ 8.04 (dd, J=10.4, 8.5 Hz, 1 H), 7.09 (dd, J=12.6, 7.0 Hz, 1 H), 2.55-2.54 (m, 1 H), 0.97-0.93 (m, 2 H), 0.69-0.66 (m, 2 H).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customPurification by flash chromatography on silica gel (0-15% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e38663c16df94e1e8524b7f57fc221d4
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09382226B2

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