Water → 3-amino-5-(4-fluorophenyl)thiophene-2-carboxylic Acid

HRID 460318

Reaction equation

HRID 460318 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[S:4][C:3]=1[C:14]([O:16]C)=[O:15].[OH-].[Li+].O.C1COCC1>CO>[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=2)[S:4][C:3]=1[C:14]([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 619692Methyl 3-amino-5-(4-fluorophenyl)thiophene-2-carboxylate

Product 1

HCID 107523413-amino-5-(4-fluorophenyl)thiophene-2-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixture consisting of 500 mg of methyl 3-amino-5-(4-fluorophenyl)thiophene-2-carboxylate, 160 mg of lithium hydroxide, 2 ml of water, 2 ml of THF and 2 ml of methanol is stirred at RT for 3 days. After dilution with 15 ml of water, unhydrolyzed ester is removed by extraction with ethyl acetate. The aqueous phase is adjusted to pH 5 using hydrochloric acid and stirred, and the precipitated solid is filtered off with suction and dried.

Workup

  1. customAfter dilution with 15 ml of water, unhydrolyzed ester is removed by extraction with ethyl acetate
  2. stirringstirred
  3. filtrationthe precipitated solid is filtered off with suction
  4. customdried

Sources & evidence

ORD record
ord-2c96ff4f637f4338b0e2cb3a6cd9e194
Source dataset
uspto-grants-2007_03
Patent number
US07196114B2

Linked notes

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