3-Hydroxybenzoic Acid → HCID 20450556, compound

HRID 358125Notes

Reaction equation

HRID 358125 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:12])[CH:8]=2)[N:3]=1.[K].[OH:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18]([OH:20])=[O:19]>CS(C)=O>[Cl:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([O:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:17]([CH:16]=1)[C:18]([OH:20])=[O:19])[CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 74203-Hydroxybenzoic AcidHCID 6075022,6-DichloroquinolineHCID 5462222Potassium

Product 1

HCID 20450556HCID 20450556, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Substantially equimolar amounts of 2,6-dichloroquinoline and the potassium salt of 3-hydroxybenzoic acid are reacted, in an inert organic solvent, e.g., dimethylsulfoxide giving 5-(6-chloro-2-quinolinoxy)benzoic acid which is nitrated, with, for example, potassium nitrate in the presence of concentrated sulfuric acid to give the corresponding 2-nitrobenzoic acid. The 2-nitrobenzoic acid is then reacted with a suitably substituted--halo compound, e.g., 2-chloropropionate, as described hereinabove.

Sources & evidence

ORD record
ord-3585672f1bf543eabe53683a2d6a9fcf
Source dataset
uspto-grants-1984_08
Patent number
US04464533

Reaction notes

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