2-(N-(3,6-dichloropyridazin-4-yl)-N-methylamino)ethanol → HCID 22030726, compound

HRID 1421040Notes

Reaction equation

HRID 1421040 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[N:8]([CH2:10][CH2:11][OH:12])[CH3:9]>[Pd].C(O)C.CO.N>[CH3:9][N:8]([CH2:10][CH2:11][OH:12])[C:7]1[CH:6]=[CH:5][N:4]=[N:3][CH:2]=1

Participants

6

Reactant 1

HCID 220307752-(N-(3,6-dichloropyridazin-4-yl)-N-methylamino)ethanol

Product 1

HCID 22030726HCID 22030726, compoundYield 91%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 222AmmoniaSolventHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of 2-(N-(3,6-dichloropyridazin-4-yl)-N-methylamino)ethanol (444 mg, 2 mmol) and 10% palladium-on-charcoal catalyst (150 mg) in ethanol (15 ml), methanol (5 ml) and aqueous ammonia (15 ml) was stirred under hydrogen at 3 atmospheres pressure for 4 hours. The catalyst was removed by filtration and the solvent removed from the filtrate by evaporation. The residue was dissolved in methylene chloride, the insoluble material was removed by filtration and the solvent was removed from the filtrate by evaporation. The residue was purified by column chromatography on neutral aluminum oxide eluting with methylene chloride/methanol (95/5 followed by 90/10). The purified product was triturated with petroleum ether, the solid product was collected by filtration and dried under vacuum to give 2-(N-methyl-N-(pyridazin-4-yl)amino)ethanol (275 mg, 91%).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent removed from the filtrate by evaporation
  3. dissolutionThe residue was dissolved in methylene chloride
  4. customthe insoluble material was removed by filtration
  5. customthe solvent was removed from the filtrate by evaporation
  6. customThe residue was purified by column chromatography on neutral aluminum oxide eluting with methylene chloride/methanol (95/5 followed by 90/10)
  7. customThe purified product was triturated with petroleum ether
  8. filtrationthe solid product was collected by filtration
  9. customdried under vacuum

Sources & evidence

ORD record
ord-99b061053a644923bdc954b9f0a1cb7f
Source dataset
uspto-grants-2000_06
Patent number
US06071921

Reaction notes

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