Hydrochloric Acid → 4-[2-[N-(4-Chlorophenyl)amino]ethoxy]benzoic acid hydrochloride

HRID 359082Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][O:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl.CCOCC>CO.O>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:20][CH:21]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Methyl 4-[2-[N-(4-chlorophenyl)amino]ethoxy]benzoate (0.4 g) was suspended in methanol (20 ml), and thereto a solution of sodium hydroxide (0.16 g) in water (5 ml) was added, and the mixture was heated with stirring at 60° C. for 3 hours. The reaction mixture was cooled, and neutralized with hydrochloric acid and concentrated under reduced pressure. After adding water thereto, the resulting residue was crushed, then, collected by filtration to give crude crystal. An equivalent amount of hydrochloric acid was added to the crude crystal in methanol, and the mixture was dried under reduced pressure to give a salt. The salt was suspended in a mixed solvent of methanol and ether, and collected by filtration to give the desired product (0.31 g). mp. 190°-193° C.

Workup

temperaturethe mixture was heated
temperatureThe reaction mixture was cooled
concentrationconcentrated under reduced pressure
additionAfter adding water
customthe resulting residue was crushed
filtrationcollected by filtration
customto give crude crystal
customthe mixture was dried under reduced pressure
customto give a salt
filtrationcollected by filtration

Sources & evidence

ORD record: ord-6d8de91afe1943239e39dfc918035043
Source dataset: uspto-grants-1991_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04999378

Reaction notes

Loading…