p-Toluenesulfonic acid → HCID 86736997, compound

HRID 1395646Notes

Reaction equation

HRID 1395646 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:22][C:23]1[C:29]([CH:30]([F:32])[F:31])=[CH:28][CH:27]=[CH:26][C:24]=1[NH2:25].[OH-].[K+]>O.CCOCC.C(O)CC>[CH3:22][C:23]1[C:29]([CH:30]([F:31])[F:32])=[CH:28][CH:27]=[CH:26][C:24]=1[NH:25][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

8

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 14797Potassium HydroxideHCID 762582-Chloronicotinic acidHCID 540584333-(Difluoromethyl)-2-methylaniline

Product 1

HCID 86736997HCID 86736997, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 10311-PropanolSolventHCID 3283Diethyl EtherSolvent

Procedure

With stirring, reflux a mixture containing 5 g. of 2-chloronicotinic acid, 0.3 g. of p-toluene sulfonic acid, 12.5 g. of 2-methyl-3-difluoromethyl aniline, and 15 ml. of n-propanol for five hours. Treat the reaction mixture with ether and 6.2 g. of potassium hydroxide dissolved in 100 ml. of water. Separate and acidify the aqueous layer with dilute hydrochloric acid to yield the product 2-(2-methyl-3-difluoromethylanilino) nicotinic acid, m.p. 232°-234° after recrystallization from acetonitrile.

Workup

  1. temperaturereflux a mixture
  2. additioncontaining 5 g
  3. customSeparate

Sources & evidence

ORD record
ord-7a91f7d968464b84a2c39f3865ee8ad6
Source dataset
uspto-grants-1980_05
Patent number
US04205073

Reaction notes

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