Pyridine → HCID 13269698, compound

HRID 2295283Notes

Reaction equation

HRID 2295283 reaction equation
[N:1]1[C:6]2[NH:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[C:10](=[O:12])[NH:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1.N1C=CC=CC=1>O1CCOCC1>[N:22]1[CH:23]=[CH:24][C:19]([C:18]([N:7]2[C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[C:10](=[O:12])[NH:11][C:5]3[CH:4]=[CH:3][CH:2]=[N:1][C:6]2=3)=[O:25])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 701695,11-Dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-oneHCID 12262826Isonicotinoyl chloride hydrochloride

Product 1

HCID 13269698HCID 13269698, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 40.4 gm (0.191 mol) of 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one, 46.0 gm (0.258 mol) of isonicotinic acid chloride hydrochloride, 42 ml (0.52 mol) of pyridine, and 600 ml of anhydrous dioxane was refluxed for three hours. After cooling, the mixture was filtered, the filter residue was taken up in 300 ml of water, and the solution obtained was extracted twice, each time with 100 ml of dichloromethane. The aqueous phase was made alkaline with sodium hydroxide solution and exhaustively extracted with methylene chloride. The methylene chloride extracts thus obtained were washed with water and dried over sodium sulphate, and the solvent was eliminated in vacuo. The residue was recrystallized from hot methanol. After washing with ether, the resulting beige-colored crystals melted at 265°-266° C.

Workup

  1. temperaturewas refluxed for three hours
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. customthe solution obtained
  5. extractionwas extracted twice
  6. extractionexhaustively extracted with methylene chloride
  7. customThe methylene chloride extracts thus obtained
  8. washwere washed with water
  9. dry with materialdried over sodium sulphate
  10. customThe residue was recrystallized from hot methanol
  11. washAfter washing with ether

Sources & evidence

ORD record
ord-f9f3dc0df33d4c3f8f64ef540fbdc168
Source dataset
uspto-grants-1984_01
Patent number
US04424226

Reaction notes

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