Hydrochloric Acid → 3-[4-(5-Nitropyridin-2-ylsulfanyl)phenyl]propionic acid

HRID 884088

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[SH:11][C:12]1[CH:22]=[CH:21][C:15]([CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C.O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([S:11][C:12]2[CH:13]=[CH:14][C:15]([CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:21][CH:22]=2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-chloro-5-nitropyridine (1.74 g, 11.0 mmol) and 4-mercaptohydrocinnamic acid (2.00 g, 11.0 mmol) in DMF (30 mL) was added potassium carbonate (4.55 g, 32.9 mmol), and the resulting solution was stirred for 1 hour at 80° C. To the reaction solution were added water and concentrated hydrochloric acid, and then cooled with ice. The precipitated solid matter was collected by filtration, to thereby yield 3.29 g of the title compound.

Workup

temperaturecooled with ice
filtrationThe precipitated solid matter was collected by filtration

Sources & evidence

ORD record: ord-5f3c21d9283e4d918f14deccd368ebf2
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236826B2

Linked notes

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