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

HRID 443641Notes

Reaction equation

HRID 443641 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+].C(O)C.O.Cl>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 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 19096565Water ethanolHCID 23468273Ethyl p-{[2-(2-naphthyloxy)ethyl]amino}benzoate

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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, m.p. 208°-211° C.

Workup

  1. additionA mixture of 3.0 g
  2. additionThe mixture is diluted with 100 ml
  3. filtrationThe mixture is filtered
  4. washthe solid washed with 50 ml
  5. customof cold ethanol-water (4:1) to give the product, m.p. 208°-211° C.

Sources & evidence

ORD record
ord-bb52f120c6ca42b69955e132f443f42f
Source dataset
uspto-grants-1981_04
Patent number
US04260816

Reaction notes

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