Sodium Hydroxide → 2-Anilino-5-phenylthiophene-3-carboxylic acid

HRID 1967157Notes

Reaction equation

[NH:1]([C:8]1[S:9][C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:11][C:12]=1[C:13]([O:15]CC)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.Cl.O.C(OCC)(=O)C>[NH:1]([C:8]1[S:9][C:10]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:11][C:12]=1[C:13]([OH:15])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of ethyl 2-anilino-5-phenylthiophene-3-carboxylate (51.7 mg, 0.160 mmol) in ethanol (3 mL) was added water (0.6 mL) and aqueous sodium hydroxide solution (2 M, 0.400 ml, 0.799 mmol). The reaction suspension was heated to 80° C. to afford a clear yellow solution; after one hour the suspension was allowed to cool to room temperature before being diluted with an aqueous hydrogen chloride solution (2 M, 1 mL), water (1.5 mL), and ethyl acetate (10 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (5 mL). The combined organic layers were combined and concentrated to afford 2-anilino-5-phenylthiophene-3-carboxylic acid.

Workup

customto afford a clear yellow solution
temperatureto cool to room temperature
customThe layers were separated
extractionthe aqueous layer was extracted with ethyl acetate (5 mL)
concentrationconcentrated

Sources & evidence

ORD record: ord-8f6e7ec8a746425fabfb7f9b73d02a28
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420695B2

Reaction notes

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