Hydrochloric Acid → HCID 14882888, compound

HRID 359094Notes

Reaction equation

HRID 359094 reaction equation
C([O:8][CH2:9][CH2:10][N:11]([CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=1)[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)C1C=CC=CC=1.Cl>C(O)C.C(OCC)(=O)C.O.[Pd]>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([N:11]([CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:24]=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:30][CH:31]=2)[CH2:10][CH2:9][OH:8])=[CH:17][CH:16]=1

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 14882887HCID 14882887, compound

Product 1

HCID 14882888HCID 14882888, compoundYield 43.1%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[3-[N-(2-Benzyloxyethyl)-N-(4-chlorophenyl)amino]propoxy]benzoic acid (3.5 g) was dissolved in a mixed solvent of ethanol (60 ml) and ethyl acetate (15 ml), and thereto were added conc. hydrochloric acid (0.7 ml) and 10 % palladium/carbon (0.35 g), and the mixture was stirred under hydrogen and atmospheric pressure at room temperature for 27 hours. The reaction mixture was diluted with water, filtered, and neutralized with lN aqueous sodium hydroxide solution, and then, the mixture was concentrated under reduced pressure. The residue was washed with water, and crystallized from about 50 % aqueous methanol and collected by filtration. The resultant was further recrystallized from a mixed solvent of ethyl acetate/n-hexane [1:10 (v/v)] to give the desired product (1.20 g). mp. 120°-122° C.

Workup

  1. filtrationfiltered
  2. concentrationthe mixture was concentrated under reduced pressure
  3. washThe residue was washed with water
  4. customcrystallized from about 50 % aqueous methanol
  5. filtrationcollected by filtration
  6. customThe resultant was further recrystallized from a mixed solvent of ethyl acetate/n-hexane [1:10 (v/v)]

Sources & evidence

ORD record
ord-ae08fbe409fe4a75a1e3ed3dfcea5e03
Source dataset
uspto-grants-1991_03
Patent number
US04999378

Reaction notes

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