Hydrochloric Acid → (R)-(methyl-phenyl-amino)-phenyl-acetic acid hydrochloride

HRID 77004Notes

Reaction equation

HRID 77004 reaction equation
C[O:2][C:3](=[O:19])[C@H:4]([N:11]([CH3:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[ClH:20].O>O1CCOCC1>[ClH:20].[CH3:18][N:11]([C@H:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:3]([OH:19])=[O:2])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 962Water2×HCID 59401128HCID 59401128, compound

Product 1

HCID 67424971(R)-(methyl-phenyl-amino)-phenyl-acetic acid hydrochlorideYield 71%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

(R)-(Methyl-phenyl-amino)-phenyl-acetic acid methyl ester (I73) (125 mg, 0.49 mmol) is dissolved in dioxane (2 mL). 37% Hydrogen chloride in water (3.00 mL, 36.5 mmol) is added and the mixture is stirred at 70° C. for 18 hours. Then a second portion of 37% hydrogen chloride in water (1.00 mL, 12.2 mmol) is added and the mixture is stirred at 70° C. for additional 36 hours. The mixture is cooled to RT and the white precipitate is filtered and washed with dioxane and Et2O to obtain intermediate I122 as a white solid (97 mg, 71% yield).

Workup

  1. stirringthe mixture is stirred at 70° C. for additional 36 hours
  2. temperatureThe mixture is cooled to RT
  3. filtrationthe white precipitate is filtered
  4. washwashed with dioxane and Et2O

Sources & evidence

ORD record
ord-ed39fb0a518e4302aeae9c79b5ecd648
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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