Hydrochloric Acid → 2-[3-Chloro-4-(4-chloropyrazol-1-yl)phenyl]propionic acid

HRID 1733020Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]([CH3:18])[C:15]([OH:17])=[O:16])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11](N)[CH:10]=[N:9]1.N([O-])=O.[Na+].[ClH:23]>[Cu]Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]([CH3:18])[C:15]([OH:17])=[O:16])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([Cl:23])[CH:10]=[N:9]1

Participants

Conditions

Temperature: -3 °C

Procedure

2.65 g (10 mmoles) of 2-[3-chloro-4-(4-aminopyrazol-1-yl)phenyl]propionic acid are dissolved in 10 ml of 25% strength hydrochloric acid, the solution is cooled to -3° C., and 1.04 g (15 mmoles) of sodium nitrite (dissolved in 5 ml of water) are added. After 10 minutes the reaction mixture is stirred into a solution of 2 g (20 mmoles) of copper(I) chloride. Heating to 100° C. ist then effected for 1 hour, followed by cooling, extraction with chloroform and purification through chromatography on silica gel (benzene/cyclohexane/glacial acetic acid 2:1:1). 2-[3-chloro-4-(4-chloropyrazol-1-yl)phenyl]propionic acid, m.p. 102°-103° C., is obtained.

Workup

temperatureHeating to 100° C.
temperatureby cooling
extractionextraction
customwith chloroform and purification through chromatography on silica gel (benzene/cyclohexane/glacial acetic acid 2:1:1)

Sources & evidence

ORD record: ord-9fd07638c9374e94bec574aea84d4aa8
Source dataset: uspto-grants-1980_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04239901

Reaction notes

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