Methyl malonyl chloride → HCID 13193388, compound

HRID 463659Notes

Reaction equation

HRID 463659 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.Cl[C:17]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[O:18]>CC(C)=O>[CH3:23][O:22][C:20]([CH2:19][C:17]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1)=[O:18])=[O:21]

Participants

4

Reactant 2

HCID 123460Methyl malonyl chlorideHCID 161928Ici 109,081

Product 1

HCID 13193388HCID 13193388, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

20.3 g (100 millimoles) of 6-(p-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone were stirred with 16.4 g (120 millimoles) of methyl chloroformylacetate and 400 ml of absolute acetone for 10 hours at room temperature. The product was filtered off under suction at 10° C., washed with cold acetone and dried at 70° C. under reduced pressure. 15.6 g (52%) of 6-[p-(methoxycarbonylacetylamino)-phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone were obtained. Mp.: 228°-230° C.

Workup

  1. filtrationThe product was filtered off under suction at 10° C.
  2. washwashed with cold acetone
  3. customdried at 70° C. under reduced pressure

Sources & evidence

ORD record
ord-1e8ed496da014b12a77f99754e703b7a
Source dataset
uspto-grants-1985_10
Patent number
US04544562

Reaction notes

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