Hydrochloric Acid → (3-Ethyl-phenylamino)-phenyl-acetic acid hydrochloride

HRID 1255019

Reaktionsgleichung

Br[CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5]CC)=[O:4].[CH2:14]([C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19])[CH3:15].C(N(C(C)C)C(C)C)C.O.[OH-].[Li+].[ClH:35]>C(#N)C.O1CCOCC1.O>[ClH:35].[CH2:14]([C:16]1[CH:17]=[C:18]([NH:19][CH:2]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:3]([OH:5])=[O:4])[CH:20]=[CH:21][CH:22]=1)[CH3:15]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

Ethyl 2-bromo-2-phenylacetate (0.29 mL, 1.64 mmol), 3-ethylaniline (0.31 mL, 2.47 mmol), and N-ethyl-N-isopropylpropan-2-amine (0.43 mL, 2.47 mmol) are dissolved in acetonitrile (5 mL) and stirred under MW irradiation at 100° C. for 1 hour (Conversion complete by UPLC/MS-UV). Lithium hydroxide hydrate (207 mg, 4.94 mmol) and water (3 mL) are added and the mixture is stirred at RT for 16 hours. 4M HCl in dioxane is added until pH 1 and the solvents are evaporated. The residue is suspended in water, sonicated, cooled at 0° C. and filtered under suction. The recovered white solid is dried under vacuum at 40° C. overnight (414 mg, 86% yield).

Aufarbeitung

stirringthe mixture is stirred at RT for 16 hours
customthe solvents are evaporated
customsonicated
temperaturecooled at 0° C.
filtrationfiltered under suction
customThe recovered white solid is dried under vacuum at 40° C. overnight (414 mg, 86% yield)

Quellen und Nachweise

ORD-Eintrag: ord-1ea8f29fd52c4d06a4837b792969390b
Quelldatensatz: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08455646B2

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