Hydrochloric Acid → 4-[(3-Phenylpropyl)amino]benzoic acid

HRID 1703089Notes

Reaction equation

HRID 1703089 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][NH:10][C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17]CC)=[O:16])=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].C(O)C.O.Cl>O>[C:1]1([CH2:7][CH2:8][CH2:9][NH:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([OH:17])=[O:16])=[CH:20][CH:21]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 13079659Ethyl 4-[(3-phenylpropyl)amino]benzoateHCID 19096565Water ethanol

Product 1

HCID 130796584-[(3-Phenylpropyl)amino]benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10 g. of ethyl p-[(3-phenylpropyl)amino]benzoate (prepared as described in Example 26), 10 g. of KOH and 200 ml. of ethanol-water (9:1) is refluxed for 4 hours. The mixture is acidified while hot with concentrated hydrochloric acid, diluted with water, cooled and filtered to give off-white crystals. Recrystallization from ethanol gives off-white crystals, m.p. 162°-163° C.

Workup

  1. additionA mixture of 10 g
  2. temperaturecooled
  3. filtrationfiltered
  4. customto give off-white crystals
  5. customRecrystallization from ethanol
  6. customgives off-white crystals, m.p. 162°-163° C.

Sources & evidence

ORD record
ord-12bd8cb153ea42cd8813f9a28269a68d
Source dataset
uspto-grants-1982_09
Patent number
US04350822

Reaction notes

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