Hydrochloric Acid → 4-(3-Chloro-6-phenyl-2-pyridyl)benzoic acid

HRID 1354416Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:14]2[CH:24]=[CH:23][C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][CH:15]=2)=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.[OH-].[Na+].O1CCCC1.Cl>O.C(O)C>[Cl:1][C:2]1[C:3]([C:14]2[CH:15]=[CH:16][C:17]([C:18]([OH:20])=[O:19])=[CH:23][CH:24]=2)=[N:4][C:5]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of ethyl 4-(3-chloro-6-phenyl-2-pyridyl)benzoate (1.00 g), 1M aqueous sodium hydroxide solution (5 ml), tetrahydrofuran (10 ml) and ethanol (20 ml) was stirred at 60° C. for 1 hr. After cooling, the reaction mixture was poured into water, and 1 M hydrochloric acid (5 ml) was added. The crystals were collected by filtration and recrystallized from tetrahydrofuran-hexane to give 4-(3-chloro-6-phenyl-2-pyridyl)benzoic acid (0.83 g, yield 91%) as colorless crystals. melting point: 254–255° C.

Workup

temperatureAfter cooling
additionwas added
filtrationThe crystals were collected by filtration
customrecrystallized from tetrahydrofuran-hexane

Sources & evidence

ORD record: ord-cc73f4eca1aa47f08e2a116b642c3749
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07223791B2

Reaction notes

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