Hydrochloric Acid → HCID 58027205, compound

HRID 909290Notes

Reaction equation

[H-].[Na+].F[C:4]1[C:9]([F:10])=[C:8]([F:11])[CH:7]=[CH:6][C:5]=1[C:12]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:13]=1[C:14]([OH:16])=[O:15].C(OCC)(=O)C.Cl>CN(C)C=O.O>[F:11][C:8]1[C:9]([F:10])=[C:4]2[C:5]([C:12]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:13]=3[C:14](=[O:16])[O:15]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

60% Sodium hydride (2.82 g, 70.5 mmol) was suspended in anhydrous N,N-dimethylformamide (60 mL), then under ice cooling, an anhydrous N,N-dimethylformamide solution (40 mL) of 2-(2,3,4-trifluorophenyl)-5-nitrobenzoic acid (Reference Compound No. 1-2-(2), 6.97 g, 23.5 mmol) was added dropwise thereto, and then the reaction mixture was stirred under nitrogen atmosphere at 80° C. for 24 hours. After cooling down, ethyl acetate (400 mL), water (400 mL) and 1N aqueous HCl solution (80 mL) were added, and then separated. The organic layer was washed with saturated brine (200 mL), dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. Chloroform was added to the obtained solid, and then filtered to give the titled reference compound (3.85 g) as a brown solid. (Yield 59%)

Workup

temperatureAfter cooling down
customseparated
washThe organic layer was washed with saturated brine (200 mL)
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was removed under reduced pressure
additionChloroform was added to the obtained solid
filtrationfiltered

Sources & evidence

ORD record: ord-9d30d217df0e436b8c26ace4d943870f
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017775B2

Reaction notes

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