Hydrochloric Acid → 2-(2-hydroxyethylamino)-4-chlorobenzoic Acid

HRID 1532428Notes

Reaction equation

Cl[C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:12]([CH2:14][NH2:15])[OH:13].Cl>>[OH:13][CH2:12][CH2:14][NH:15][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 700Ethanolamine

HCID 57872,4-Dichlorobenzoic Acid

Product 1

HCID 212519912-(2-hydroxyethylamino)-4-chlorobenzoic AcidYield 97%

Procedure

First, 2,4-dichlorobenzoic acid (VI) (19.1 g) and cupric chloride (200 mg) were added to ethanolamine (XI) (36.6 g) and the solution was reacted at 80 to 90° C. for 4.5 hours. After the reaction, the pH of the reaction solution was adjusted to 1 by addition of concentrated hydrochloric acid, and then the resulting precipitate was collected by filtration to give 20.9 g of 2-(2-hydroxyethylamino)-4-chlorobenzoic acid (IX) (yield, 97%).

Workup

customthe solution was reacted at 80 to 90° C. for 4.5 hours
customAfter the reaction
filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record: ord-25b37b61a6db4b83ae9f1efa892cf67f
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06201121B1

Reaction notes

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