Salicylic Acid → HCID 19429159, compound

HRID 1078204Notes

Reaction equation

HRID 1078204 reaction equation
[Cl:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([Cl:9])[N:3]=1.[C:10](O)(=[O:18])[C:11]1[C:12](=[CH:14][CH:15]=[CH:16][CH:17]=1)[OH:13].S(Cl)(Cl)=O.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[C:7]([NH:8][C:10](=[O:18])[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[OH:13])=[CH:6][CH:5]=[C:4]([Cl:9])[N:3]=1

Participants

7

Reactant 4

HCID 338Salicylic AcidHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 1128462,6-Dichloro-3-pyridylamine

Product 1

HCID 19429159HCID 19429159, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 60.3g (0.37 mole) 2,6-dichloro-3-aminopyridine and salicylic acid 61g (0.44 mole) in 300 mL of toluene were heated to reflux for one hour. The reaction mixture was cooled at 90° C. and 34.2 ml (0.47 mole) of thionyl chloride was slowly added. After the addition the reaction mixture was refluxed for 3 hours, then cooled to room temperature. To the reaction mixture was added a solution containing 20g NaOH in 740 mL of H2O. The organic phase was separated and washed with water. The organic phase was treated with charcoal, filtered and the filtrate treated with CO2, the brownish precipitate was filtered off. Recrystallization from isopropyl alcohol gave 63.3g (60.5%) mp 179°-186° C.

Workup

  1. temperaturewere heated
  2. temperatureto reflux for one hour
  3. additionAfter the addition the reaction mixture
  4. temperaturewas refluxed for 3 hours
  5. temperaturecooled to room temperature
  6. additionTo the reaction mixture was added a solution
  7. customThe organic phase was separated
  8. washwashed with water
  9. additionThe organic phase was treated with charcoal
  10. filtrationfiltered
  11. additionthe filtrate treated with CO2
  12. filtrationthe brownish precipitate was filtered off
  13. customRecrystallization from isopropyl alcohol
  14. customgave 63.3g (60.5%) mp 179°-186° C.

Sources & evidence

ORD record
ord-b2ad2a29385b41d3b813b69a76142ca1
Source dataset
uspto-grants-1996_08
Patent number
US05547951

Reaction notes

Loading…