Hydrochloric Acid → 2,4-Difluoro-6-((2-fluoro-4-iodophenyl)amino)benzoic acid

HRID 1808954Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1808954
F[C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([F:12])[C:3]=1[C:4]([OH:6])=[O:5].[F:13][C:14]1[CH:20]=[C:19]([I:21])[CH:18]=[CH:17][C:15]=1[NH2:16].[NH2-].[Li+].Cl>C(#N)C>[F:12][C:7]1[CH:8]=[C:9]([F:11])[CH:10]=[C:2]([NH:16][C:15]2[CH:17]=[CH:18][C:19]([I:21])=[CH:20][C:14]=2[F:13])[C:3]=1[C:4]([OH:6])=[O:5]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 24532Lithium amideHCID 1856942-Fluoro-4-iodoanilineHCID 5203732,4,6-Trifluorobenzoic acid

Produkt 1

HCID 670515602,4-Difluoro-6-((2-fluoro-4-iodophenyl)amino)benzoic acidAusbeute 59,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

2,4,6-Trifluorobenzoic acid (643 mg, 3.65 mmol) and 2-fluoro-4-iodoaniline (1.0 g, 4.22 mmol) were taken into acetonitrile (30 mL) followed by addition of lithium amide (290 mg, 12.7 mmol) and the mixture was heated to 60° C. under a nitrogen atmosphere for one hour. On cooling to room temperature the mixture was added to 1 N aqueous hydrochloric acid (100 mL) and the precipitate formed was collected by filtration and washed once with water then hexanes and dried in vacuo to give 2,4-difluoro-6-[(2-fluoro-4-iodophenyl)amino]benzoic acid (849 mg, 59% yield) as a tan solid. 1H-NMR (400 MHz, D6-DMSO): 13.72 (br s, 1H), 9.46 (s, 1H), 7.75 (d, 1H), 7.56 (d, 1H) 7.28 (tr, 1H), 6.73-6.67 (m, 1H), 6.53 (d, 1H).

Aufarbeitung

  1. temperatureOn cooling to room temperature the mixture
  2. customthe precipitate formed
  3. filtrationwas collected by filtration
  4. washwashed once with water
  5. dry with materialhexanes and dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1d43b0559f3149f4beb61721dd7ce915
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362002B2

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