Hydrochloric Acid → (E)-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-hydroxy-acrylic acid

HRID 2116679

Reaction equation

C(N/[C:5](=[CH:9]/[C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[C:13]([NH2:20])=[C:12]([Cl:21])[CH:11]=1)/[C:6]([OH:8])=[O:7])(=O)C.Cl.[OH2:23]>CN1C(=O)CCC1>[NH2:20][C:13]1[C:14]([C:16]([F:19])([F:18])[F:17])=[CH:15][C:10](/[CH:9]=[C:5](/[OH:23])\[C:6]([OH:8])=[O:7])=[CH:11][C:12]=1[Cl:21]

Participants

Conditions

Temperature: 130 °C

Procedure

51.0 g (158 mmol) (E)-2-acetylamino-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-acrylic acid, dissolved in 408 ml NMP, were combined with 612 ml aqueous 4-molar hydrochloric acid solution and stirred for 3 hours at a bath temperature of 130° C. stirred. The reaction mixture was cooled and poured onto 2000 ml of water with stirring. The precipitate formed was suction filtered, washed with 400 ml of water, dried overnight at 60° C. and recrystallised from 1000 ml boiling toluene.

Workup

stirringstirred
temperatureThe reaction mixture was cooled
stirringwith stirring
customThe precipitate formed
filtrationfiltered
washwashed with 400 ml of water
customdried overnight at 60° C.
customrecrystallised from 1000 ml

Sources & evidence

ORD record: ord-1865c91b6b5b40e686352f2c345f66c0
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07439237B2

Linked notes

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