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

HRID 1255019Notes

Reaction equation

HRID 1255019 reaction equation
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]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 114753-EthylanilineHCID 81531DiisopropylethylamineHCID 97780Ethyl bromophenylacetateHCID 168937Lithium hydroxide, monohydrate

Product 1

HCID 67425860(3-Ethyl-phenylamino)-phenyl-acetic acid hydrochlorideYield 86%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-1ea8f29fd52c4d06a4837b792969390b
Source dataset
uspto-grants-2013_06
Patent number
US08455646B2

Reaction notes

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