Hydrochloric Acid → HCID 14882889, compound

HRID 359096Notes

Reaction equation

HRID 359096 reaction equation
[C:1]([CH2:4][CH2:5][N:6]([CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][CH:19]=1)[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)([OH:3])=[O:2].[OH-].[Na+].Cl>CO.O>[C:1]([CH2:4][CH2:5][N:6]([CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:26][CH:27]=1)[C:7]1[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=1)([OH:3])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15086626HCID 15086626, compound

Product 1

HCID 14882889HCID 14882889, compoundYield 65.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 4-[3-[N-(2-carboxyethyl)-N-(4-chlorophenyl)amino]propoxy]benzoate (1.37 g) was dissolved in methanol (20 ml) and thereto was added a solution of sodium hyroxide (0.42 g) in water (4 ml), and the mixture was heated with stirring at 60° C. for 23 hours. After the reaction mixture was cooled, a neutralizing amount of conc. hydrochloric acid was added thereto, then, concentrated under reduced pressure. The residue was allowed to stand in water (pH; about 4.5) and the resulting crystal was collected by filtration, washed with water, and recrystallized from about 30 % aqueous methanol to give the desired product (0.87 g). mp. 132°-133° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureAfter the reaction mixture was cooled
  3. concentrationconcentrated under reduced pressure
  4. filtrationthe resulting crystal was collected by filtration
  5. washwashed with water
  6. customrecrystallized from about 30 % aqueous methanol

Sources & evidence

ORD record
ord-c64f3a2904474c9c9ce49088cc08376f
Source dataset
uspto-grants-1991_03
Patent number
US04999378

Reaction notes

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