Hydrochloric Acid → p-{[2-(2-Naphthyloxy)ethyl]amino}benzoic acid

HRID 2051920Notes

Reaction equation

HRID 2051920 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][CH2:13][NH:14][C:15]1[CH:25]=[CH:24][C:18]([C:19]([O:21]CC)=[O:20])=[CH:17][CH:16]=1.[OH-].[K+].Cl>C(O)C.O.O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][CH2:13][NH:14][C:15]1[CH:25]=[CH:24][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 23468273Ethyl p-{[2-(2-naphthyloxy)ethyl]amino}benzoate

Product 1

HCID 23468295p-{[2-(2-Naphthyloxy)ethyl]amino}benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

A mixture of 3.0 g of ethyl p-{[2-(2-naphthyloxy)-ethyl]amino}benzoate, and 3.0 g of potassium hydroxide in 200 ml of ethanol-water (95:5) is refluxed for 3 hours. The mixture is diluted with 100 ml of water and brought to pH 6.0 with concentrated hydrochloric acid. The mixture is filtered and the solid washed with 50 ml of water and 20 ml of cold ethanol-water (4:1) to give the product, mp 208°-211° C.

Workup

  1. temperatureis refluxed for 3 hours
  2. filtrationThe mixture is filtered
  3. washthe solid washed with 50 ml of water and 20 ml of cold ethanol-water (4:1)
  4. customto give the product, mp 208°-211° C.

Sources & evidence

ORD record
ord-f6ebdbaed33e415fbc59f1491b6d7e68
Source dataset
uspto-grants-1980_01
Patent number
US04182776

Reaction notes

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