Butylamine → HCID 47174299, compound

HRID 2042716Notes

Reaction equation

HRID 2042716 reaction equation
[Cl:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[N:5]=[CH:6][C:7]=1[Cl:8].[CH2:11]([NH2:15])[CH2:12][CH2:13][CH3:14]>C(#N)C>[CH2:11]([NH:15][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[N:5]=[CH:6][C:7]=1[Cl:8])[CH2:12][CH2:13][CH3:14].[CH2:11]([NH:15][C:7]1[CH:6]=[N:5][N:4]([CH3:9])[C:3](=[O:10])[C:2]=1[Cl:1])[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 8007ButylamineHCID 1204623(2H)-Pyridazinone, 4,5-dichloro-2-methyl-

Product 2

HCID 47174299HCID 47174299, compoundHCID 67994474HCID 67994474, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4,5-dichloro-2-methylpyridazin-3(2H)-one (358 mg, 2 mmol) and butan-1-amine (585 mg, 8 mmol) in acetonitrile was refluxed for 16 hours. The mixture was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, washed with water, brine, dried with MgSO4, filtered, and concentrated. Purification of the residue by chromatography (hexanes-EtOAc 1:1) afforded 170 mg of 4-(butylamino)-5-chloro-2-methylpyridazin-3(2H)-one and 260 mg of 5-(butylamino)-4-chloro-2-methylpyridazin-3(2H)-one. MS (ESI) m/z 215 (M+H)+.

Workup

  1. temperaturewas refluxed for 16 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the residue by chromatography (hexanes-EtOAc 1:1)

Sources & evidence

ORD record
ord-a849a6112dd7494a8af507ebf067f005
Source dataset
uspto-grants-2013_11
Patent number
US08586596B2

Reaction notes

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