4-Hydroxybenzoic Acid → HCID 19745161, compound

HRID 981849Notes

Reaction equation

HRID 981849 reaction equation
OC1C=CC(C(O)=O)=CC=1.S(Cl)(Cl)=O.[OH:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1.[NH2:25][C:26]1[CH:27]=[C:28]([CH:34]=[CH:35][CH:36]=1)[C:29]([O:31][CH2:32][CH3:33])=[O:30]>N1C=CC=CC=1>[CH2:32]([O:31][C:29]([C:28]1[CH:27]=[C:26]([NH:25][C:20](=[O:21])[C:19]2[CH:23]=[CH:24][C:16]([OH:15])=[CH:17][CH:18]=2)[CH:36]=[CH:35][CH:34]=1)=[O:30])[CH3:33]

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 11400Ethyl 3-aminobenzoateHCID 24386Thionyl ChlorideHCID 110519074-hydroxybenzoyl Chloride

Product 1

HCID 19745161HCID 19745161, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

4-Hydroxybenzoic acid can be converted into the corresponding acid chloride upon treatment with thionyl chloride in pyridine. The reaction of equimolar amounts of 4-hydroxybenzoyl chloride and ethyl 3-aminobenzoate in pyridine yields N-(3-ethoxycarbonylphenyl)-4-hydroxybenzamide which can be transferred into ethyl 5-{[3-(ethoxycarbonylphenyl)amino]carbonyl}-2-hydroxybenzenepropanoate according to the procedure of Example 92A. Alkylation of this phenol according to the procedure of Example 60 followed by hydrolysis of the resulting diester by the method of Example 56 will provide the title compound.

Sources & evidence

ORD record
ord-2696c76c620144a599eea5f9af3c70a9
Source dataset
uspto-grants-1991_02
Patent number
US04992576

Reaction notes

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