Hydrochloric Acid → Methyl 4-(cyclohexyloxy)-2-(4-fluoroanilino)benzoate

HRID 2191665Notes

Reaction equation

[F:1][C:2]1[CH:19]=[CH:18][C:5]([NH:6][C:7]2[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:8]=2[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:26]1(Br)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.Cl>C(OCC)(=O)C.CN(C)C=O>[CH:26]1([O:17][C:15]2[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([NH:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:19][CH:18]=3)[CH:16]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

Conditions

Temperature: 80 °C

Procedure

To N,N-dimethylformamide 3.0 mL solution of methyl 2-(4-fluoroanilino)-4-hydroxybenzoate 0.30 g were added potassium carbonate 0.16 g and cyclohexyl bromide 0.42 mL at room temperature, and it was stirred at 80° C. for 8 hours. After the reaction mixture was cooled to room temperature,11.0 mol/L hydrochloric acid and ethyl acetate were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B(spherical type), eluent; hexane:ethyl acetate=8:1] to give methyl 4-(cyclohexyloxy)-2-(4-fluoroanilino)benzoate 40 mg of colorless oil.

Workup

temperatureAfter the reaction mixture was cooled to room temperature
customThe organic layer was separated
washafter washing with saturated sodium chloride aqueous solution
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-24861d9307df45db9c1d5ac014aca61e
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08327467B2

Reaction notes

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