Hydrochloric Acid → 4-[(7-Phenylheptyl)amino]benzoic acid

HRID 2052501Notes

Reaction equation

HRID 2052501 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]2[CH:25]=[CH:24][C:18]([C:19]([O:21]CC)=[O:20])=[CH:17][CH:16]=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][CH2:12][CH2:13][NH:14][C:15]2[CH:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[CH:24][CH:25]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 13079667Ethyl 4-[(7-phenylheptyl)amino]benzoateHCID 19096565Water ethanol

Product 1

HCID 130796664-[(7-Phenylheptyl)amino]benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5 g. of ethyl p-[(7-phenylheptyl)amino]benzoate (prepared as described in Example 34), 5 g. of KOH and 50 ml. of ethanol-water (9:1) is refluxed for 3.5 hours. The mixture is acidified while hot with concentrated hydrochloric acid, diluted with H2O, chilled and filtered. The solid is washed with H2O to give off-white crystals, m.p. 123°-126° C. Recrystallization from ethanol gives tan crystals, m.p. 123.5°-125° C.

Workup

  1. additionA mixture of 5 g
  2. temperaturechilled
  3. filtrationfiltered
  4. washThe solid is washed with H2O
  5. customto give off-white crystals, m.p. 123°-126° C
  6. customRecrystallization from ethanol
  7. customgives tan crystals, m.p. 123.5°-125° C.

Sources & evidence

ORD record
ord-3cdf21e544b5494f9280a93b2850a555
Source dataset
uspto-grants-1980_01
Patent number
US04185115

Reaction notes

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