Toluene → {2-[(3-Aminopyridin-2-yl)amino]phenyl}(3-chlorophenyl)methanone

HRID 2412978Notes

Reaction equation

HRID 2412978 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[CH:7]=1)=[O:5].[NH2:17][C:18]1[C:19](Cl)=[N:20][CH:21]=[CH:22][CH:23]=1.C1(C)C=CC=CC=1>C(Cl)Cl>[NH2:17][C:18]1[C:19]([NH:1][C:2]2[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=2[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[CH:7]=2)=[O:5])=[N:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 805282-Chloro-3-pyridylamineHCID 12231012Methanone, (2-aminophenyl)(3-chlorophenyl)-

Product 1

HCID 15586656{2-[(3-Aminopyridin-2-yl)amino]phenyl}(3-chlorophenyl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
180 °C

Procedure

A stirred mixture of 35 g (0.152 mole) of 2-amino-3'-chlorobenzophenone and 23.4 g (0.182 mole) of 3-amino-2-chloropyridine was heated at 180° C. for 2 hr. The hot melt was allowed to cool to 110° C., after which 100 ml of hot toluene was added dropwise with vigorous stirring. The mixture was allowed to cool while stirring to 30° C. and 50 ml of methylene chloride was added. After stirring for an additional 1/2 hour, the mixture was filtered and the filter cake suspended in methylene chloride with stirring for 1/2 hr and methylene chloride was separated by filtration. The filter cake containing the product (25.4 g) was partially dissolved in hot methanol (total volume 150 ml) and 50% aqueous sodium hydroxide was added until the mixture was basic. Ice water was added and the solution was extracted with methylene chloride. This methylene chloride extract was washed with water and dried over magnesium sulfate and evaporated to dryness. The residue was dissolved in isopropyl alcohol and boiled with charcoal. The mixture was filtered, reduced in volume to give a first crop of crystals weighing 16 g (33%). A portion of the crystals was recrystallized from isopropyl alcohol to give a brick red solid melting 119°-120° C.

Workup

  1. temperatureto cool to 110° C.
  2. temperatureto cool
  3. stirringAfter stirring for an additional 1/2 hour
  4. filtrationthe mixture was filtered
  5. stirringwith stirring for 1/2 hr
  6. custommethylene chloride was separated by filtration
  7. additionThe filter cake containing the product (25.4 g)
  8. dissolutionwas partially dissolved in hot methanol (total volume 150 ml)
  9. addition50% aqueous sodium hydroxide was added until the mixture
  10. additionIce water was added
  11. extractionthe solution was extracted with methylene chloride
  12. extractionThis methylene chloride extract
  13. washwas washed with water
  14. dry with materialdried over magnesium sulfate
  15. customevaporated to dryness
  16. dissolutionThe residue was dissolved in isopropyl alcohol
  17. filtrationThe mixture was filtered
  18. customto give a first crop of crystals
  19. customA portion of the crystals was recrystallized from isopropyl alcohol
  20. customto give a brick red solid
  21. custommelting 119°-120° C.

Sources & evidence

ORD record
ord-aea8a17ad1524dc383bd0c8e57a9bcf7
Source dataset
uspto-grants-1985_01
Patent number
US04495183

Reaction notes

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