Hydrochloric Acid → 4-[(5-Phenylpentyl)amino]benzoic acid

HRID 2052497Notes

Reaction equation

HRID 2052497 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]2[CH:23]=[CH:22][C:16]([C:17]([O:19]CC)=[O:18])=[CH:15][CH:14]=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][CH2:10][CH2:11][NH:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[CH:22][CH:23]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 13079663Ethyl 4-[(5-phenylpentyl)amino]benzoateHCID 19096565Water ethanol

Product 1

HCID 130796624-[(5-Phenylpentyl)amino]benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7 g. of ethyl p-[(5-phenylpentyl)amino]benzoate (prepared as described in Example 46), 7 g. of potassium hydroxide and 100 ml. of ethanol-water (9:1) is refluxed for 3 hours. The mixture is acidified with concentrated hydrochloric acid while hot, diluted with water, cooled and filtered. The solid is washed with water to give white crystals, m.p. 141°-143° C. Recrystallization from ethanol gives white crystals, m.p. 142°-144° C.

Workup

  1. additionA mixture of 7 g
  2. temperaturecooled
  3. filtrationfiltered
  4. washThe solid is washed with water
  5. customto give white crystals, m.p. 141°-143° C
  6. customRecrystallization from ethanol
  7. customgives white crystals, m.p. 142°-144° C.

Sources & evidence

ORD record
ord-6e33f9175e104786bbe2146fd4bac5f1
Source dataset
uspto-grants-1980_01
Patent number
US04185115

Reaction notes

Loading…