Sodium Hydroxide → 4-[3-[N-(3,4-Methylenedioxyphenyl)amino]propoxy]benzoic acid

HRID 359080Notes

Reaction equation

[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([NH:10][CH2:11][CH2:12][CH2:13][O:14][C:15]3[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[CH:17][CH:16]=3)=[CH:4][C:3]=2[O:2]1.[OH-].[Na+]>CO.O>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([NH:10][CH2:11][CH2:12][CH2:13][O:14][C:15]3[CH:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[CH:23][CH:24]=3)=[CH:4][C:3]=2[O:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

Methyl 4-[3-[N-(3,4-methylenedioxyphenyl)amino]propoxy]benzoate (1.5 g) was suspended in methanol (20 ml), and thereto a solution of sodium hydroxide (0.55 g) in water (5 ml) was added, then, the mixture was heated with stirring at 60° C. for 13 hours. After the reaction solution was concentrated under reduced pressure, the residue was washed with ether several times, and further thereto were added water and a neutralization amount of conc. hydrochloric acid. The resulting crystal was collected by filtration to give the desired product (0.99 g). mp. 164°-167° C. (decomposed).

Workup

temperaturethe mixture was heated
concentrationAfter the reaction solution was concentrated under reduced pressure
washthe residue was washed with ether several times
additionfurther thereto were added water
filtrationThe resulting crystal was collected by filtration

Sources & evidence

ORD record: ord-dd0c9972358b422e812e9e9f44b8f5f1
Source dataset: uspto-grants-1991_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04999378

Reaction notes

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