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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 640929Generated: October 30, 2026

4-Aminobenzoic Acid → 4-[(2-Oxo-6-{3-[(thiophene-2-carbonyl)-amino]-benzoyl}-1,2-dihydro-indol-3-ylidenemethyl)-amino]-benzoic acid

https://huagongshe.com/reaction/640929

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-Aminobenzoic AcidHCID 978—
ReactantN-[3-[3-(hydroxymethylidene)-2-oxo-1H-indole-6-carbonyl]phenyl]thiophene-2-carboxamideHCID 178517289—
SolventTetrahydrofuranHCID 8028—
Product4-[(2-Oxo-6-{3-[(thiophene-2-carbonyl)-amino]-benzoyl}-1,2-dihydro-indol-3-ylidenemethyl)-amino]-benzoic acidHCID 6869842081%

Reaction Conditions

Temperature65 °C

Reaction Steps

A small screw cap test tube was charged with Thiophene-2-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 45, 80 mg, 0.2049 mmol) and THF (2 mL). To the resulting solution was added 4-Amino-benzoic acid (34 mg, 0.248 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature. The room temperature reaction mixture was concentrated in vacuo. The solid residue was recrystallized from EtOAc (5 mL) and Hexanes (2 mL) yielding the title compound in 81% yield (0.085 g, 0.1668 mmol).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07692005B2
Source datasetuspto-grants-2010_04
ORD IDord-aa0ae4b4c6df4b4eb72e7dd245b686fc
Source noteuspto-grants-2010_04