Potassium Hydroxide → 4-[(2-Fluoro-4-iodophenyl)amino]thiophene-3-carboxylic acid

HRID 1717609Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1717609
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11]([C:15]([O:17]C)=[O:16])=[CH:12][S:13][CH:14]=1.[OH-].[K+]>C(O)C.O.O>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11]([C:15]([OH:17])=[O:16])=[CH:12][S:13][CH:14]=1

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 66617354Methyl 4-[(2-fluoro-4-iodophenyl)amino]thiophene-3-carboxylate

Produkt 1

HCID 666174654-[(2-Fluoro-4-iodophenyl)amino]thiophene-3-carboxylic acidAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 19096565Water ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of methyl 4-[(2-fluoro-4-iodophenyl)amino]thiophene-3-carboxylate (0.74 g, 1.96 mmol) in the solution of potassium hydroxide (0.3 g) in ethanol/water (4 ml/4 ml) was heated up to 60° C. and stirred at this temperature for 30 min. The mixture was cooled to room temperature, diluted with 4 ml of water and extracted with ether. The water layer was acidified with 1 N HCl to pH 2, the product precipitated and was filtered off, washed several times with water and dried in vacuo to afford 4-[(2-fluoro-4-iodophenyl)amino]thiophene-3-carboxylic acid (0.59 g, 83%). 1H NMR (d6-DMSO): 13.20 (s, 1H), 9.13 (s, 1H), 8.35 (d, 1H), 7.62 (dd, 1H), 7.48-7.38 (m, 2H), 7.11 (s, 1H); MS (EI) for C11H7FINO2S: 362 (MH−).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ether
  3. customthe product precipitated
  4. filtrationwas filtered off
  5. washwashed several times with water
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3f34aaab4792440682d78d4f51106141
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803839B2

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