Acetic Acid → 2-Amino-6-chloro-5-(4-chlorophenyl)pyridine-3-carboxylic acid

HRID 1980324Notes

Reaction equation

HRID 1980324 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[CH:6][C:5]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[C:4]([Cl:20])[N:3]=1.O1CCOCC1.[OH-].[Na+].C(O)(=O)C>O>[NH2:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[C:4]([Cl:20])[N:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 13502857HCID 13502857, compound

Product 1

HCID 135028582-Amino-6-chloro-5-(4-chlorophenyl)pyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Amino-6-chloro-5-(4-chlorophenyl)-3-pyridinecarboxylic acid, ethyl ester (0.3 gram) was partially dissolved in 3 ml water and 3 ml dioxane and then 0.2 gram of sodium hydroxide was added. The reaction mixture was refluxed for 11/2-2 hours and, after the mixture was neutralized with glacial acetic acid, a precipitate formed which was collected and washed with water, yield approximately 250 mg, m.p. 280°-284° C. dec.

Workup

  1. temperatureThe reaction mixture was refluxed for 11/2-2 hours
  2. customa precipitate formed which
  3. customwas collected
  4. washwashed with water, yield approximately 250 mg, m.p. 280°-284° C. dec.

Sources & evidence

ORD record
ord-c192615c2b224956a2e4d2028d963e7f
Source dataset
uspto-grants-1985_04
Patent number
US04508722

Reaction notes

Loading…