Aniline → 2-Anilinonicotinic acid

HRID 2194524Notes

Reaction equation

HRID 2194524 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>[I-].[K+].C1(C)C=CC=CC=1>[C:12]1([NH:11][C:2]2[N:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 6115AnilineHCID 762582-Chloronicotinic acid

Product 1

HCID 14817992-Anilinonicotinic acidYield 110.4%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

5.0 g (31.7 mmol) of 2-chloronicotinic acid, 5.9 g (63.5 mmol) of aniline, and 0.1 g of potassium iodide were heated up 140° C., and toluene (30 mL) was added to this reaction mixture. The resulting mixture was stirred for 2 hours at 100° C. The reaction mixture was cooled, and then the solvent was distilled off. Chloroform was added to the residue, and insoluble materials were filtered off. The filtrate was concentrated, and thus 7.5 g of the title compound was obtained as crude pale yellow crystals (yield: quantitative).

Workup

  1. temperatureThe reaction mixture was cooled
  2. distillationthe solvent was distilled off
  3. additionChloroform was added to the residue, and insoluble materials
  4. filtrationwere filtered off
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b448fedb2bdd432086c1b9d6a67b55a2
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

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