2-Methoxypropanoyl chloride → HCID 13193373, compound

HRID 463650Notes

Reaction equation

HRID 463650 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.[CH3:16][O:17][CH:18]([CH3:22])[C:19](Cl)=[O:20]>O1CCCC1>[CH3:16][O:17][CH:18]([CH3:22])[C:19]([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:20]

Participants

4

Reactant 2

HCID 924952-Methoxypropanoyl chlorideHCID 161928Ici 109,081

Product 1

HCID 13193373HCID 13193373, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.0 g (24.6 millimoles) of 6-(p-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone and 3.6 g (29.4 millimoles) of 2-methoxypropionyl chloride in 150 ml of absolute tetrahydrofuran were refluxed for 2 hours, while stirring. The mixture was evaporated down, the residue was stirred with water and the product was filtered off under suction, washed with water, dried, and recrystallized from propanol. 4.0 g (56%) of 6-[p-(2-methoxypropionylamino)-phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone were obtained as colorless crystals. Mp.: 193°-194° C.

Workup

  1. customThe mixture was evaporated down
  2. stirringthe residue was stirred with water
  3. filtrationthe product was filtered off under suction
  4. washwashed with water
  5. customdried
  6. customrecrystallized from propanol

Sources & evidence

ORD record
ord-bf5b75907ac1495380c71944da3860a1
Source dataset
uspto-grants-1985_10
Patent number
US04544562

Reaction notes

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