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

HRID 237351Notes

Reaction equation

HRID 237351 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-].[Li+]>O1CCCC1.CO.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 3939Lithium HydroxideHCID 66617354Methyl 4-[(2-fluoro-4-iodophenyl)amino]thiophene-3-carboxylate

Product 1

HCID 666174654-[(2-Fluoro-4-iodophenyl)amino]thiophene-3-carboxylic acidYield 80.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Methyl 4-(2-Fluoro-4-iodo-phenylamino)-thiophene-3-carboxylate (270 mg, 0.72 mmol) was dissolved in a mixture of tetrahydrofuran:methanol (6:1, 3 mL) and a solution of lithium hydroxide (0.1 g, 4.2 mmol) in 1 mL of water was added. The solution was stirred at room temperature for 18 hours and the solvent was concentrated. The residue was dissolved in 5 mL of water and the solution was acidified to pH 1 with 1N HCl. The resulting solid was filtered and dried in vacuo to provide 210 mg (79% yield) of 4-(2-fluoro-4-iodo-phenylamino)-thiophene-3-carboxylic acid. MS (EI) for C11H7FINO2S: 364 (MH+).

Workup

  1. concentrationthe solvent was concentrated
  2. dissolutionThe residue was dissolved in 5 mL of water
  3. filtrationThe resulting solid was filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-9130bc57961d426f8ea7fe9fe907ab46
Source dataset
uspto-grants-2014_02
Patent number
US08642584B2

Reaction notes

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