Hydrochloric Acid → HCID 23141413, compound

HRID 558333Notes

Reaction equation

[F:1][C:2]([F:27])([F:26])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:25])[C:12]2[CH:13]=[C:14]([CH:20]=[CH:21][C:22]=2[O:23][CH3:24])[C:15]([O:17]CC)=[O:16])=[CH:6][CH:5]=1.[OH-].[K+].Cl>CO>[F:1][C:2]([F:26])([F:27])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:25])[C:12]2[CH:13]=[C:14]([CH:20]=[CH:21][C:22]=2[O:23][CH3:24])[C:15]([OH:17])=[O:16])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Ethyl N-(4-trifluoromethoxyphenyl)-4-methoxy-isophthalamate (51 mg) obtained in step E was dissolved in 2 mL of methanol, and 0.8 mL of a 20% aqueous solution of potassium hydroxide was added. The resulting solution was stirred for 30 minutes at 80° C., and then cooled to room temperature. One M hydrochloric acid (3 mL) was used to adjust the solution to pH of about 3. Then, the resulting aqueous solution was extracted with ethyl acetate. The respective organic layers were combined, whereafter the combined organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was separated by filtration, and washed with ethyl acetate. The filtrate and the washings were combined, and ethyl acetate was distilled off under reduced pressure to obtain 48 mg (100%) of N-(4-trifluoromethoxyphenyl)-4-methoxyisophthalamic acid.

Workup

temperaturecooled to room temperature
extractionThen, the resulting aqueous solution was extracted with ethyl acetate
washwas washed with a saturated aqueous solution of sodium chloride
dry with materialdried over anhydrous sodium sulfate
customThe anhydrous sodium sulfate was separated by filtration
washwashed with ethyl acetate
distillationethyl acetate was distilled off under reduced pressure

Sources & evidence

ORD record: ord-f18bdecab7264292b6fb9b92b397bc3f
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063046B2

Reaction notes

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