Hydrochloric Acid → 7-Fluoro-1-methyl-5-nitro-1,3-dihydro-indol-2-one

HRID 2114869Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2114869
F[C:2]1[C:7]([F:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH2:12][C:13]([OH:15])=O.[CH3:16][NH2:17].O.Cl>CS(C)=O>[F:8][C:7]1[CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=[C:3]2[C:2]=1[N:17]([CH3:16])[C:13](=[O:15])[CH2:12]2

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6329MethylamineHCID 11951676(2,3-Difluoro-5-nitrophenyl)acetic acid

Produkt 1

HCID 119516757-Fluoro-1-methyl-5-nitro-1,3-dihydro-indol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

Crude (2,3-difluoro-5-nitrophenyl)acetic acid (12, 1.00 g, 0.00461 mol) and a 40% solution of methylamine in water (3 eq., 1.20 ml, 0.0138 mol) are mixed in DMSO (5 ml) and stirred at 45° C. for 1 hour. 2N Hydrochloric acid (20 ml) is added in one portion and the mixture stirred at room temperature for 1 hour. The reaction mixture is extracted with ethyl acetate and the extract washed with saturated aqueous sodium bicarbonate and brine, dried (MgSO4) and evaporated. The residue is purified by flash column chromatography (50% ethyl acetate/hexane) to give the title compound as a solid. HPLC r.t. 4.4 min.

Aufarbeitung

  1. stirringthe mixture stirred at room temperature for 1 hour
  2. extractionThe reaction mixture is extracted with ethyl acetate
  3. washthe extract washed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue is purified by flash column chromatography (50% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-b457b77ac1fc43cfaa66861c5d21f889
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07435751B2

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