2-Amino-5-(4-chlorophenyl)pyridine-3-carboxylic acid → 5-(4-Chlorophenyl)pyridin-2-amine

HRID 1980307Notes

Reaction equation

HRID 1980307 reaction equation
[NH2:1][C:2]1[C:7](C(O)=O)=[CH:6][C:5]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[CH:4][N:3]=1>[Cu].N1C2C(=CC=CC=2)C=CC=1>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 132426432-Amino-5-(4-chlorophenyl)pyridine-3-carboxylic acid

Product 1

HCID 132426445-(4-Chlorophenyl)pyridin-2-amine

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Conditions

Temperature
230 °C

Procedure

2-Amino-5-(4-chlorophenyl)-3-pyridinecarboxylic acid (1.0 gram), copper powder (0.2 gram), and 10 ml quinoline were heated in an oil bath at 205° C. After 21/2 hours, the temperature was raised to 230° C. for an additional hour. A solid precipitate formed which was collected and then washed with ethyl acetate. The solution was then stripped and the residue chromatographed on 300 ml of silica gel. The gum-like solid was applied to the top of the column with ether and then eluted with additional ether until all the quinoline was removed. Elution with ethyl acetate very slowly produced a brown solid which was recrystallized from methanol-water giving tan plate-like crystals, yield 400 mg, m.p. 122°-124° C.

Workup

  1. customA solid precipitate formed which
  2. customwas collected
  3. washwashed with ethyl acetate
  4. customthe residue chromatographed on 300 ml of silica gel
  5. washeluted with additional ether until all the quinoline
  6. customwas removed
  7. washElution with ethyl acetate
  8. customvery slowly produced a brown solid which
  9. customwas recrystallized from methanol-water giving tan plate-like crystals, yield 400 mg, m.p. 122°-124° C.

Sources & evidence

ORD record
ord-a9f839bbede141e0ab1c75b9ac4bef1f
Source dataset
uspto-grants-1985_04
Patent number
US04508722

Reaction notes

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