Pyridine → HCID 86615033, compound

HRID 1890626Notes

Reaction equation

HRID 1890626 reaction equation
[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:28]=[CH:27][C:18]([C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=O)=[CH:17][CH:16]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2].Cl.[NH2:30][OH:31].N1C=CC=CC=1>C(O)C.C(Cl)(Cl)Cl>[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:28]=[CH:27][C:18]([C:19](=[N:30][OH:31])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:17][CH:16]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 11326145HCID 11326145, compound

Product 1

HCID 86615033HCID 86615033, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

Compound 1 (0.300 g, 0.812 mmol) was dissolved in ethanol (10 mL), and hydroxylamine monohydrochloride (0.113 g, 1.63 mmol) and pyridine (0.145 mL, 1.79 mmol) was added to the solution, followed by stirring at 60° C. for 3.5 hours. The reaction mixture was diluted with chloroform, and sequentially washed with water, 0.5 mol/L hydrochloric acid, and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The crude crystals were recrystallized from ethanol to obtain Compound 3 (0.213 g, yield 68%).

Workup

  1. washsequentially washed with water, 0.5 mol/L hydrochloric acid, and saturated brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-a4dccb8096c54138b4e0790c91caa6da
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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