Hydrochloric Acid → HCID 14882899, compound

HRID 359104Notes

Reaction equation

HRID 359104 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:13][CH2:12][CH2:11][CH:10]2[CH2:14][O:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH:9]2[CH2:13][CH2:12][CH2:11][CH:10]2[CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:24][CH:25]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15086644HCID 15086644, compound

Product 1

HCID 14882899HCID 14882899, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 4-[2-[N-(4-chlorophenyl)amino]cyclopentan-1-ylmethoxy]benzoate (2.57 g) was dissolved in methanol (40 ml) and thereto was added a solution of sodium hydroxide (0.86 g) in water (8 ml), and the mixture was heated with stirring at 60° C. for 14 hours. The reaction mixture was cooled and thereto was added conc. hydrochloric acid (1.87 ml), then, the mixture was concentrated under reduced pressure. The residue was washed with water and about 50 % aqueous methanol was added thereto, and the mixture was heated. The mixture was allowed to stand, and the resulting crystal was collected by filtration to give the desired product (1.72 g). mp. 153°-156° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureThe reaction mixture was cooled
  3. concentrationthe mixture was concentrated under reduced pressure
  4. washThe residue was washed with water and about 50 % aqueous methanol
  5. additionwas added
  6. temperaturethe mixture was heated
  7. filtrationthe resulting crystal was collected by filtration

Sources & evidence

ORD record
ord-f636ed31d16347d69af6dfd0db118b25
Source dataset
uspto-grants-1991_03
Patent number
US04999378

Reaction notes

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