Hydrochloric Acid → HCID 14882895, compound

HRID 359101Notes

Reaction equation

HRID 359101 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH:10]([CH3:23])[CH2:11][O:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][CH:10]([CH3:23])[CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[CH:21][CH:22]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15086629HCID 15086629, compound

Product 1

HCID 14882895HCID 14882895, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 4-[3 [N-[4-chlorophenyl)amino]-2-methylpropoxy]benzoate (2.80 g) was dissolved in methanol (30 ml) and thereto was added a solution of sodium hydroxide (1.00 g) in water (8 ml), and the mixture was heated with stirring at 60° C. for 15 hours. The reaction mixture was cooled and thereto was added conc. hydrochloric acid (2.20 ml), and the mixture was concentrated under reduced pressure. To the residue was added water and it was crushed, and was collected by filtration. The resultant was dissolved in methanol, and filtered. Water (about half volume of the filtrate) was added to the filtrate gradually, and the resulting crystal was collected by filtration to give the desired product (2.16 g). mp. 148°-150° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureThe reaction mixture was cooled
  3. concentrationthe mixture was concentrated under reduced pressure
  4. additionTo the residue was added water and it
  5. customwas crushed
  6. filtrationwas collected by filtration
  7. dissolutionThe resultant was dissolved in methanol
  8. filtrationfiltered
  9. additionWater (about half volume of the filtrate) was added to the filtrate gradually
  10. filtrationthe resulting crystal was collected by filtration

Sources & evidence

ORD record
ord-65bda433f8f949ccb5c97dbdaca0ebc4
Source dataset
uspto-grants-1991_03
Patent number
US04999378

Reaction notes

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