Hydrochloric Acid → 4-{[3-(4-Chlorophenyl)propyl]amino}benzoic acid

HRID 2052520Notes

Reaction equation

HRID 2052520 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][NH:11][C:12]2[CH:22]=[CH:21][C:15]([C:16]([O:18]CC)=[O:17])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[OH-].[K+].C(O)C.Cl>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:21][CH:22]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 13079692Ethyl 4-{[3-(4-chlorophenyl)propyl]amino}benzoate

Product 1

HCID 130796914-{[3-(4-Chlorophenyl)propyl]amino}benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 16.3 g. of ethyl 4-[3-(p-chlorophenyl)propylamino]benzoate, 16.3 g. of potassium hydroxide and 200 ml. of 95% ethanol is refluxed for 3 hours. The mixture is diluted with 100 ml. of water brought to pH 6 with concentrated hydrochloric acid. Chilling and filtering gave 15 g. of white crystals. Recrystallization from ethanol gave 8.6 g. of white crystals, m.p. 191°-192° C.

Workup

  1. additionA mixture of 16.3 g
  2. additionThe mixture is diluted with 100 ml
  3. temperatureChilling
  4. filtrationfiltering
  5. customgave 15 g
  6. customRecrystallization from ethanol
  7. customgave 8.6 g

Sources & evidence

ORD record
ord-827cf6daf3cb43fdb27a1921f706f6e7
Source dataset
uspto-grants-1980_01
Patent number
US04185115

Reaction notes

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