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

HRID 1809012Notes

Reaction equation

HRID 1809012 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
60 °C

Procedure

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−).

Workup

  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

Sources & evidence

ORD record
ord-ca15f6955d9f48c2a12647ade942d2be
Source dataset
uspto-grants-2013_01
Patent number
US08362002B2

Reaction notes

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