Hydrochloric Acid → Phenyl-o-methylphenylamino-acetic acid hydrochloride

HRID 76981

Reaktionsgleichung

Reaktionsgleichung von HRID 76981
Br[CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5]CC)=[O:4].[NH2:14][C:15]1[C:16]([CH3:21])=[CH:17][CH:18]=[CH:19][CH:20]=1.CCN(C(C)C)C(C)C.O.[OH-].[Li+].[ClH:34]>C(#N)C.O1CCOCC1.O>[ClH:34].[C:8]1([CH:2]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[C:3]([OH:5])=[O:4])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 7242O-ToluidineHCID 81531DiisopropylethylamineHCID 97780Ethyl bromophenylacetateHCID 168937Lithium hydroxide, monohydrate

Produkt 1

HCID 67124826Phenyl-o-methylphenylamino-acetic acid hydrochlorideAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Ethyl 2-bromo-2-phenylacetate (0.28 mL, 1.64 mmol), ortho-toluidine (0.26 mL, 2.47 mmol) and DIPEA (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 is about 1, then the solvents are evaporated, the residue is suspended in water, sonicated, cooled at 0° C. and the resulting solid is recovered by filtration and dried under vacuum to get intermediate I86 as a off-white solid (290 mg, 63% yield).

Aufarbeitung

  1. stirringthe mixture is stirred at RT for 16 hours
  2. customthe solvents are evaporated
  3. customsonicated
  4. temperaturecooled at 0° C.
  5. filtrationthe resulting solid is recovered by filtration
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-99cdd32759ab4cd194d408358df71df5
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835682B2

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