3-Chloroaniline → Nicotinic Acid

HRID 704933Notes

Reaction equation

HRID 704933 reaction equation
Cl[C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.ClC1C=C(C=CC=1)N>O>[N:3]1[CH:4]=[CH:5][CH:6]=[C:7]([C:8]([OH:10])=[O:9])[CH:2]=1

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 762582-Chloronicotinic acid

Product 1

HCID 938Nicotinic AcidYield 188.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 2-chloro-3-pyridinecarboxylic acid (78.75 g, 0.500 mol), 3-chloroaniline (127.6 g, 1.00 mol), paratoluenesulfonic acid. H2O (8.5 g, 45 mmol), and H2O (500 mL) was refluxed 4 hrs. The solids dissolved, and after 1 hr, the solution gave a precipitate. The cooled mixture was filtered, and the collected yellow solid was washed with cold H2O and was dried (60°) to give 2-[3-chlorophenyl)amino]-3-pyridinecarboxylic acid (116.0 g, 93.3%), mp 197°-199° C.

Workup

  1. dissolutionThe solids dissolved
  2. customthe solution gave a precipitate
  3. filtrationThe cooled mixture was filtered
  4. washthe collected yellow solid was washed with cold H2O
  5. customwas dried (60°)

Sources & evidence

ORD record
ord-939468bbb4b741d3a5bd95bfd434833a
Source dataset
uspto-grants-1991_01
Patent number
US04988705

Reaction notes

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