Ethyl Acetate → HCID 9907917, compound

HRID 392530Notes

Reaction equation

HRID 392530 reaction equation
Br[CH2:2][CH2:3][CH2:4][NH:5][C:6]1[C:7](=[O:13])[NH:8][N:9]=[CH:10][C:11]=1[Cl:12].[CH3:14][NH:15][CH2:16][CH2:17][C:18]1[CH:27]=[CH:26][C:23]([O:24][CH3:25])=[C:20]([O:21][CH3:22])[CH:19]=1.C(=O)([O-])O.[K+].C(OCC)(=O)C>CC(C)=O.C(N(CC)CC)C>[Cl:12][C:11]1[CH:10]=[N:9][NH:8][C:7](=[O:13])[C:6]=1[NH:5][CH2:4][CH2:3][CH2:2][N:15]([CH2:16][CH2:17][C:18]1[CH:27]=[CH:26][C:23]([O:24][CH3:25])=[C:20]([O:21][CH3:22])[CH:19]=1)[CH3:14]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 77039N-Methylhomoveratrylamine2×HCID 516893Potassium BicarbonateHCID 109344284-(3-bromopropylamino)-5-chloro-3(2H)-pyridazinone2×

Product 1

HCID 9907917HCID 9907917, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A mixture of 10.66 g (0.04 mole) of 4-(3-bromopropylamino)-5-chloro-3(2H)-pyridazinone (II), 10.0 g (0.05 mole) of N-methyl-homoveratryl amine (VI) and 8 g of potassium hydrogen carbonate is suspended in 80 cm3 of acetone. The reaction mixture is refluxed for 8 to 12 hours. The reaction is followed by TLC (eluent: ethyl acetate: acetone:triethylamine==10:10:0.5 (II Rf=0.76), (VI Rf=0.14), (I Rf=0.47)). The mixture is filtered while hot, washed with acetone and the mother liquor is evaporated in vacuo. To the residue 50 cm3 of ethyl acetate are added. The possibly separated inorganic substance is filtered off and the filtrate is evaporated again. The residual viscous, oily product (14 to 15 g) is triturated twice with 50 cm3 of hot water in order to remove the unreacted starting substance of the formula (VI). The warm aqueous solution is decanted. The oily residue is dissolved in methanol and dried over magnesium sulfate. Upon adding a small amount of diisopropyl ether and cooling the mixture white porous substance separates. Thus 9 g (59.0%) of crude product are obtained. M.p.: 89-90° C. After recrystallization from diisopropyl ether 7.0 g (46.0%) of the title compound are obtained.

Workup

  1. temperatureThe reaction mixture is refluxed for 8 to 12 hours
  2. filtrationThe mixture is filtered while hot,
  3. washwashed with acetone
  4. customthe mother liquor is evaporated in vacuo
  5. additionTo the residue 50 cm3 of ethyl acetate are added
  6. filtrationThe possibly separated inorganic substance is filtered off
  7. customthe filtrate is evaporated again
  8. customThe residual viscous, oily product (14 to 15 g) is triturated twice with 50 cm3 of hot water in order
  9. customto remove the
  10. customThe warm aqueous solution is decanted
  11. dissolutionThe oily residue is dissolved in methanol
  12. dry with materialdried over magnesium sulfate
  13. additionUpon adding a small amount of diisopropyl ether
  14. temperaturecooling the mixture white porous substance separates

Sources & evidence

ORD record
ord-f6e5f7ce27df484783ef9ffb7433f8cc
Source dataset
uspto-grants-2004_10
Patent number
US06800758B1

Reaction notes

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