Water → HCID 19913682, compound

HRID 477809Notes

Reaction equation

HRID 477809 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][NH:7][N:8]3[C:15](=[O:16])[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:13][C:12]([C:23]([N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[O:24])=[C:9]32)=[CH:4][CH:3]=1.[CH2:31](I)[CH3:32].[OH-].[Na+].O>ClCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:31]([N:7]1[CH2:6][C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:9]2=[C:12]([C:23]([N:25]3[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)=[O:24])[CH:13]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:15](=[O:16])[N:8]12)[CH3:32]

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 14798Sodium HydroxideHCID 19913693HCID 19913693, compound

Product 1

HCID 19913682HCID 19913682, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

1.26 g of 4-[(10-chloro-6,7-dihydro-4-oxo-3-phenyl-4H-pyrido[2,1-a]phthalazin-1-yl)carbonyl]morpholine are dissolved in 30 ml of dichloromethane under argon, whereupon 1.01 g of tetrabutylammonium hydrogen sulfate, 1.4 g of ethyl iodide and 1.45 ml of 50 percent sodium hydroxide solution are added thereto and the mixture is stirred at room temperature until the reaction has finished. Three (3) ml of water are added thereto. The organic phase is separated and dried, and the solvent is removed in vacuo. The residue is chromatographed on silica gel. After recrystallization there is obtained 4-[(6-ethyl-10-chloro-6,7-dihydro-4-oxo-3-phenyl-4H-pyrido[2,1-a]phthalazin-1-yl)carbonyl]morpholine as yellow crystals of m.p. 288°-289° (acetonitrile).

Workup

  1. additionare added
  2. customThe organic phase is separated
  3. customdried
  4. customthe solvent is removed in vacuo
  5. customThe residue is chromatographed on silica gel
  6. customAfter recrystallization

Sources & evidence

ORD record
ord-6f798b33104b4b98808b0443a5ba8329
Source dataset
uspto-grants-1989_12
Patent number
US04889854

Reaction notes

Loading…