Toluene → 5-Chloro-6-hydroxynicotinoyl chloride

HRID 1651288Notes

Reaction equation

HRID 1651288 reaction equation
[Cl:1][C:2]1[C:3]([OH:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](O)=[O:8].C1(C)C=CC=CC=1.S(Cl)([Cl:21])=O>>[Cl:1][C:2]1[C:3]([OH:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([Cl:21])=[O:8]

Participants

4

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 178524771HCID 178524771, compound

Product 1

HCID 1785211275-Chloro-6-hydroxynicotinoyl chloride

Procedure

6.3 g (36 mmol) of 5-chloro-6-hydroxynicotinic acid are heated under reflux in 60 ml of thionyl chloride for 4 hours. After the volatile constituents have been stripped off, 50 ml of toluene are added and the mixture is evaporated again. Colorless crystals, yield 6.9 g (quantitative), melting point: >250° C.

Workup

  1. customthe mixture is evaporated again

Sources & evidence

ORD record
ord-a4769c91c1a94a718858c870eb4fb1c1
Source dataset
uspto-grants-1990_05
Patent number
US04927938

Reaction notes

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