Phenethylamine → 6-{p-[3-(2-phenylethylamino)-propionylamino]-phenyl}-4,5-dihydro-3(2H)-pyridazinone

HRID 1110329Notes

Reaction equation

HRID 1110329 reaction equation
Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH2:14][CH2:15][C:16](=[O:19])[NH:17][N:18]=2)=[CH:9][CH:8]=1)=[O:5].[C:20]1([CH2:26][CH2:27][NH2:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[C:20]1([CH2:26][CH2:27][NH:28][CH2:2][CH2:3][C:4]([NH:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH2:14][CH2:15][C:16](=[O:19])[NH:17][N:18]=3)=[CH:9][CH:8]=2)=[O:5])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 1001PhenethylamineHCID 133851966-[p-(3-chloropropionylamino)-phenyl]-4,5-dihydro-3(2H)-pyridazinone

Product 1

HCID 221550006-{p-[3-(2-phenylethylamino)-propionylamino]-phenyl}-4,5-dihydro-3(2H)-pyridazinoneYield 36.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

11.18 g (40 millimoles) of 6-[p-(3-chloropropionylamino)-phenyl]-4,5-dihydro-3(2H)-pyridazinone in 250 ml of ethanol were initially taken and 26.5 g (220 millimoles) of 2-phenylethylamine were added dropwise, after which the mixture was refluxed for 6 hours. Insoluble material was filtered off, the solvent was stripped off and the mother liquor was then crystallized by adding acetone. The product was recrystallized twice from methanol to give 5.3 g of 6-{p-[3-(2-phenylethylamino)-propionylamino]-phenyl}-4,5-dihydro-3(2H)-pyridazinone.HCl of melting point 269°-270° C.

Workup

  1. temperatureafter which the mixture was refluxed for 6 hours
  2. filtrationInsoluble material was filtered off
  3. customthe mother liquor was then crystallized
  4. additionby adding acetone
  5. customThe product was recrystallized twice from methanol

Sources & evidence

ORD record
ord-3a62cfe99e60446291be3ce3b3617f88
Source dataset
uspto-grants-1990_12
Patent number
USRE033476

Reaction notes

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