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

HRID 543602Notes

Reaction equation

HRID 543602 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[NH2:16][C:17]1[C:18](Cl)=[N:19][CH:20]=[CH:21][CH:22]=1>C(Cl)Cl>[NH2:16][C:17]1[C:18]([NH:1][C:2]2[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=2[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:5])=[N:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 760802-AminobenzophenoneHCID 805282-Chloro-3-pyridylamine

Product 1

HCID 15586652{2-[(3-Aminopyridin-2-yl)amino]phenyl}(phenyl)methanoneYield 3.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
180 °C

Procedure

A stirred mixture of 39.4 g (0.20 mole) of 2-aminobenzophenone and 28.3 g (0.22 mole) of 3-amino-2-chloropyridine was heated at 180° C. under nitrogen atmosphere for 1.5 hr. The mixture was allowed to cool somewhat and 200 ml of methylene chloride was added slowly. After stirring for 3 hr and standing overnight at room temperature, 40.1 g of solid was filtered off and recrystallized twice from methanolisopropyl ether giving 4.3 g, presumably the hydrochloride salt; m.p. 187°-90° C. This solid was dissolved in a mixture of water-methanol, basified with 3 N sodium hydroxide and extracted with methylene chloride. The combined methylene chloride extracts were dried over magnesium sulfate and evaporated under reduced pressure. The residue was recrystallized from isopropyl ether (charcoal) to give 2.1 g of product; m.p. 91°-3° C. Drying prior to analysis was overnight at room temperature/0.02 mm Hg.

Workup

  1. temperatureto cool somewhat
  2. waitstanding overnight at room temperature
  3. filtration40.1 g of solid was filtered off
  4. customrecrystallized twice from methanolisopropyl ether giving 4.3 g
  5. dissolutionThis solid was dissolved in a mixture of water-methanol
  6. extractionextracted with methylene chloride
  7. dry with materialThe combined methylene chloride extracts were dried over magnesium sulfate
  8. customevaporated under reduced pressure
  9. customThe residue was recrystallized from isopropyl ether (charcoal)

Sources & evidence

ORD record
ord-5a6f07489cb043bab1330942d2fdad88
Source dataset
uspto-grants-1984_05
Patent number
US04447361

Reaction notes

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