Hydroxylamine HCl → HCID 136344373, compound

HRID 2409969Notes

Reaction equation

HRID 2409969 reaction equation
[Cl-].[OH:2][NH3+:3].C(=O)([O-])O.[Na+].[CH3:9][C:10]1[CH:18]=[C:17]2[C:13]([C:14]([CH2:25][C:26]3[N:31]=[C:30]([C:32]#[N:33])[CH:29]=[CH:28][CH:27]=3)=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[NH:16]2)=[CH:12][CH:11]=1>C(O)C>[CH3:9][C:10]1[CH:18]=[C:17]2[C:13]([C:14]([CH2:25][C:26]3[N:31]=[C:30]([C:32](=[N:3][OH:2])[NH2:33])[CH:29]=[CH:28][CH:27]=3)=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[NH:16]2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 21645Hydroxylamine HClHCID 516892Sodium BicarbonateHCID 86703289HCID 86703289, compound

Product 1

HCID 136344373HCID 136344373, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a suspension of hydroxylammonium chloride (27.6 mg) in ethanol (1 mL) was added sodium hydrogen carbonate (33.4 mg), and this mixture was heated under reflux for 45 minutes. Then, a solution of 6-(6-methyl-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carbonitrile (61 mg) in ethanol (1.3 mL) was added dropwise thereto under ice-cooling, and the mixture was heated under reflux for additional 3.5 hours. The reaction mixture was left to be cooled and concentrated under reduced pressure. To the residue was added water, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (60.8 mg). 1H-NMR (CDCl3) δ ppm: 2.47 (3H, s), 4.42 (2H, s), 5.64 (2H, br s), 6.48-6.84 (1H, br), 6.90-6.97 (1H, m), 7.08-7.14 (1H, m), 7.18-7.23 (1H, m), 7.32-7.49 (4H, m), 7.52 (1H, t, J=7.8 Hz), 7.54-7.61 (2H, m), 7.66-7.74 (1H, m), 8.06 (1H, br s). ESI-MS (m/z): 357 (M+H)+

Workup

  1. temperaturethis mixture was heated
  2. temperatureunder reflux for 45 minutes
  3. temperatureunder ice-cooling
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for additional 3.5 hours
  6. waitThe reaction mixture was left
  7. temperatureto be cooled
  8. concentrationconcentrated under reduced pressure
  9. additionTo the residue was added water
  10. extractionfollowed by extraction with ethyl acetate
  11. washThe organic layer was washed with saturated brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-812dbec3ae8041dba7bfeb760a5c274f
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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