Hydrochloric Acid → 5-(5-bromo-2-chlorobenzamido)-1-phenyl-1H-pyrazole-3-carboxylic acid

HRID 522127Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:27])=[C:6]([CH:26]=1)[C:7]([NH:9][C:10]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:13]=[C:12]([C:21]([O:23]CC)=[O:22])[CH:11]=1)=[O:8].[Li+].[OH-].Cl>CCO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:27])=[C:6]([CH:26]=1)[C:7]([NH:9][C:10]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:13]=[C:12]([C:21]([OH:23])=[O:22])[CH:11]=1)=[O:8]

Participants

Conditions

Temperature: 40 °C

Procedure

To a suspension of ethyl 5-(5-bromo-2-chlorobenzamido)-1-phenyl-1H-pyrazole-3-carboxylate (Preparation 13, 2.81 mmol, 1.26 g) in EtOH (14 mL) was added 0.5M aqueous LiOH solution (14.04 mmol, 336 mg in 28 mL of water). The reaction was stirred at 40° C. for 3 hours before acidifying to pH=5 with 1N HCl. The resulting precipitate was filtered and dried to afford the title compound (1.13 g, 97%).

Workup

filtrationThe resulting precipitate was filtered
customdried

Sources & evidence

ORD record: ord-5c16b4dc2bbd42ea9644597d54fef0c1
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328096B2

Reaction notes

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