Triethylamine → HCID 58128682, compound

HRID 2088467Notes

Reaction equation

HRID 2088467 reaction equation
CC1[N:3]([C:8]2[CH:9]=[C:10]([C:15]3[C:16](=[O:22])[N:17]([CH3:21])[N:18]=[CH:19][CH:20]=3)[CH:11]=[CH:12][C:13]=2[CH3:14])C(C)=CC=1.Cl.ON.C(N(CC)CC)C>CCO.O>[NH2:3][C:8]1[CH:9]=[C:10]([C:15]2[C:16](=[O:22])[N:17]([CH3:21])[N:18]=[CH:19][CH:20]=2)[CH:11]=[CH:12][C:13]=1[CH3:14]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 58128717HCID 58128717, compound

Product 1

HCID 58128682HCID 58128682, compoundYield 51.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-[3-(2,5-dimethyl-pyrrol-1-yl)-4-methyl-phenyl]-2-methyl-2H-pyridazin-3-one (1.05 g, 3.57 mmol) in EtOH (20 ml) and water (10 ml) was added hydroxyl amine hydrochloride (2.49 g, 35.79 mmol) and triethyl amine (1.0 ml, 7.16 mmol). The mixture was heated at reflux for 24 hours. The solvent was evaporated to dryness under reduced pressure and the rsidue was partitioned between water and EtOAc. The organic layer was separated and washed with water and brine, dried over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification of the residue by flash chromatography (hex:EtOAc/1:1) gave 0.396 g (51%) of 4-(3-amino-4-methyl-phenyl)-2-methyl-2H-pyridazin-3-one as a yellow solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 hours
  3. customThe solvent was evaporated to dryness under reduced pressure
  4. customthe rsidue was partitioned between water and EtOAc
  5. customThe organic layer was separated
  6. washwashed with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure
  10. customPurification of the residue by flash chromatography (hex:EtOAc/1:1)

Sources & evidence

ORD record
ord-f913e801d4644ac884dbdb78965ef90d
Source dataset
uspto-grants-2013_05
Patent number
US08435990B2

Reaction notes

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