[2-[(3-Amino-2-pyridinyl)amino]-4-chlorophenyl]phenylmethanone → 9-chloro-6-phenyl-11H-pyrido[2,3-b][1,4]benzodiazepine

HRID 543616Notes

Reaction equation

HRID 543616 reaction equation
[NH2:1][C:2]1[C:3]([NH:8][C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=O)=[N:4][CH:5]=[CH:6][CH:7]=1>C1(C)C=CC=CC=1>[Cl:15][C:13]1[CH:12]=[CH:11][C:10]2[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:1][C:2]3[CH:7]=[CH:6][CH:5]=[N:4][C:3]=3[NH:8][C:9]=2[CH:14]=1

Participants

3

Reactant 1

HCID 15586654[2-[(3-Amino-2-pyridinyl)amino]-4-chlorophenyl]phenylmethanone2×

Product 1

HCID 155866969-chloro-6-phenyl-11H-pyrido[2,3-b][1,4]benzodiazepine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 6.6 g (0.02 mole) of [2-[(3-amino-2-pyridyl)amino]-4-chlorophenyl]-(phenyl)methanone (Intermediate 2) in 200 ml of toluene was heated at reflux over night under nitrogen atmosphere. The reaction mixture was filtered hot and the filtrate heated back to reflux temperature. The precipitate formed in cooling to room temperature was separated by filtration and recrystallized from benzene and dried 4 hr at 97°-98° C./0.1 mm Hg and over night at room temperature/0.1 mm Hg to give 3.7 g; m.p. 250.5° to 252° C. Elemental analysis for carbon was high and the product was redried at 139° C. (xylenes in drying pistol) for 8 hr. Although the carbon analysis remained high, the proton nuclear magnetic resonance spectrum and mass spectrum was consistent with the proposed structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux over night under nitrogen atmosphere
  3. filtrationThe reaction mixture was filtered hot
  4. temperaturethe filtrate heated back
  5. temperatureto reflux temperature
  6. customThe precipitate formed
  7. customwas separated by filtration
  8. customrecrystallized from benzene
  9. customdried 4 hr at 97°-98° C./0.1 mm Hg
  10. customover night at room temperature/0.1 mm Hg to give 3.7 g
  11. customthe product was redried at 139° C.
  12. dry with material(xylenes in drying pistol) for 8 hr

Sources & evidence

ORD record
ord-61300a3c402b4ac881509794668454e8
Source dataset
uspto-grants-1984_05
Patent number
US04447361

Reaction notes

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