Hydrochloric Acid → 4-[13-(4-Chlorophenyl)-12-tridecynylamino]benzoic acid

HRID 2057643Notes

Reaction equation

HRID 2057643 reaction equation
ClC1C=CC(C[CH:9]([NH:21][C:22]2[CH:32]=[CH:31][C:25]([C:26]([O:28]CC)=[O:27])=[CH:24][CH:23]=2)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=CC=1.[OH-].[K+].[CH2:35](O)[CH3:36].[ClH:38]>O>[Cl:38][C:11]1[CH:12]=[CH:13][C:35]([C:36]#[C:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][NH:21][C:22]2[CH:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[CH:31][CH:32]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 54279737Ethyl 4-[13-(4-chlorophenyl)-12-tridecylamino]benzoate

Product 1

HCID 203309694-[13-(4-Chlorophenyl)-12-tridecynylamino]benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 4 g. sample of ethyl 4-[13-(4-chlorophenyl)-12-tridecylamino]benzoate is hydrolyzed with 1.6 g. 85% potassium hydroxide in 60 ml. 95% ethanol by refluxing the solution for 5 hours. The solution is cooled, diluted with 100 ml. water and acidified to pH 4.5 with 37% hydrochloric acid. The precipitate is collected, dried in vacuo and crystallized from acetone to yield the title compound as a white powder.

Workup

  1. temperatureThe solution is cooled
  2. additiondiluted with 100 ml
  3. customThe precipitate is collected
  4. customdried in vacuo
  5. customcrystallized from acetone

Sources & evidence

ORD record
ord-febc975e5be742cea81f97208dd0eb00
Source dataset
uspto-grants-1980_07
Patent number
US04211783

Reaction notes

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