Diethyl Ether → HCID 19898591, compound

HRID 1196481Notes

Reaction equation

HRID 1196481 reaction equation
[O:1]=[C:2]1[N:7]2[N:8]=[CH:9][C:10]3[C:15]([C:6]2=[C:5](C(O)=O)[CH:4]=[C:3]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3.S(Cl)(Cl)=O.[CH3:29][N:30]([CH3:33])[CH:31]=[O:32].C[CH2:35][O:36]CC>C1(C)C=CC=CC=1>[OH:36][CH:35]1[CH2:33][N:30]([C:31]([C:5]2[CH:4]=[C:3]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:2](=[O:1])[N:7]3[N:8]=[CH:9][C:10]4[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=4)[C:6]=23)=[O:32])[CH2:29]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 156408254-Oxo-3-phenyl-4H-pyrido[2,1-a]phthalazine-1-carboxylic acid

Product 1

HCID 19898591HCID 19898591, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.68 g of 4-oxo-3-phenyl-4H-pyrido[2,1-a]phthalazine-1-carboxylic acid are suspended in 80 ml of toluene with the exclusion of moisture, whereupon 5.1 ml of thionyl chloride and 0.2 ml of N,N-dimethylformamide are added thereto and the mixture is stirred at room temperature for 2 hours. The reaction mixture is evaporated in vacuo; the residue is taken up in toluene whereupon the solution is again evaporated in vacuo. The thus-obtained pure carboxylic acid chloride is taken up in 90 ml of dioxan, whereupon there are added thereto in succession 6.52 ml of triethylamine and 1.4 g of 3-hydroxyazetidine hydrochloride. The mixture is stirred at room temperature until the reaction has finished. After removing the solvent in vacuo the residue is treated with a mixture of 200 ml of water and 100 ml of saturated aqueous sodium chloride solution, whereupon the mixture is cooled to about 2° and stirred for 30 minutes. The crystals are filtered off under suction and washed twice with 15 ml of water. The thus-obtained crystals are dried at 70° in vacuo. The aqueous phase is extracted three times with methylene chloride; the combined organic phases are washed once with 50 ml of water, dried over sodium sulfate, filtered and evaporated. The crystals are combined with the material obtained above and stirred in 150 ml of ether for 30 minutes. The ether is removed by filtration and the yellow crystals are dried. There is obtained 3-hydroxy-1-[(4-oxo-3-phenyl-4H-pyrido[2,1-a]phthalazin-1 yl)carbonyl]azetidine of m.p. 260°-264° (dec.).

Workup

  1. additionare added
  2. customThe reaction mixture is evaporated in vacuo
  3. customis again evaporated in vacuo
  4. additionare added
  5. stirringThe mixture is stirred at room temperature until the reaction
  6. customAfter removing the solvent in vacuo the residue
  7. additionis treated with a mixture of 200 ml of water and 100 ml of saturated aqueous sodium chloride solution, whereupon the mixture
  8. temperatureis cooled to about 2°
  9. stirringstirred for 30 minutes
  10. filtrationThe crystals are filtered off under suction
  11. washwashed twice with 15 ml of water
  12. customThe thus-obtained crystals are dried at 70° in vacuo
  13. extractionThe aqueous phase is extracted three times with methylene chloride
  14. washthe combined organic phases are washed once with 50 ml of water
  15. dry with materialdried over sodium sulfate
  16. filtrationfiltered
  17. customevaporated
  18. customobtained above and
  19. customThe ether is removed by filtration
  20. customthe yellow crystals are dried

Sources & evidence

ORD record
ord-af0a7582be9a4cab8fbbb72333e85b98
Source dataset
uspto-grants-1992_05
Patent number
US05114934

Reaction notes

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