Benzylamine → HCID 14003355, compound

HRID 1906663Notes

Reaction equation

HRID 1906663 reaction equation
Br[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]([CH3:20])[CH2:15][C:16](=[O:19])[NH:17][N:18]=2)=[CH:9][CH:8]=1)=[O:5].[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)CC>[CH2:21]([NH:28][CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]([CH3:20])[CH2:15][C:16](=[O:19])[NH:17][N:18]=2)=[CH:9][CH:8]=1)=[O:5])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 140033506-[4-(3-bromopropionamido)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone

Product 1

HCID 14003355HCID 14003355, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A suspension of 6-[4-(3-bromopropionamido)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone (120 g, 0.355 mol) and benzylamine (152 g, 1.47 mol) in n-propanol (800 ml) was stirred under reflux for 16 hours. The reaction mixture was filtered whilst hot and white solid was collected, which was washed with ether to remove excess benzylamine. The crude material was boiled with ethanol (300 ml) for 2 hours; the mixture was cooled and filtered. The resulting white solid was washed with ether and dried to give 6-[4-(3-benzylaminopropionamido)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone (114 g, 88%) as the hydrobromide salt m.p. 279°-285° C.

Workup

  1. temperatureunder reflux for 16 hours
  2. filtrationThe reaction mixture was filtered whilst hot and white solid
  3. customwas collected
  4. washwhich was washed with ether
  5. customto remove excess benzylamine
  6. temperaturethe mixture was cooled
  7. filtrationfiltered
  8. washThe resulting white solid was washed with ether
  9. customdried

Sources & evidence

ORD record
ord-f57a53c01d7a41e3ad12b309cd167aab
Source dataset
uspto-grants-1987_03
Patent number
US04652563

Reaction notes

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