Hydroxylamine HCl → HCID 136344372, compound

HRID 2409968Notes

Reaction equation

HRID 2409968 reaction equation
[Cl-].[OH:2][NH3+:3].C(=O)([O-])O.[Na+].[CH3:9][O:10][C:11]1[CH:19]=[C:18]2[C:14]([C:15]([CH2:26][C:27]3[N:32]=[C:31]([C:33]#[N:34])[CH:30]=[CH:29][CH:28]=3)=[C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[NH:17]2)=[CH:13][CH:12]=1>CS(C)=O.O>[CH3:9][O:10][C:11]1[CH:19]=[C:18]2[C:14]([C:15]([CH2:26][C:27]3[N:32]=[C:31]([C:33](=[N:3][OH:2])[NH2:34])[CH:30]=[CH:29][CH:28]=3)=[C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[NH:17]2)=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 21645Hydroxylamine HClHCID 516892Sodium BicarbonateHCID 86703287HCID 86703287, compound

Product 1

HCID 136344372HCID 136344372, compoundYield 105.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of hydroxylammonium chloride (891 mg) in dimethylsulfoxide (5 mL) was added sodium hydrogen carbonate (1.29 g), and this mixture was stirred at 50° C. for 75 minutes. Then, a solution of 6-(6-methoxy-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carbonitrile (435 mg) in dimethylsulfoxide (1.4 mL) was added dropwise thereto, followed by stirring at 50° C. for 24 hours. The reaction mixture was left to be cooled and diluted with water, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain the title compound (504 mg). 1H-NMR (CDCl3) δ ppm: 3.86 (3H, s), 4.40 (2H, s), 5.63 (2H, br s), 6.43-6.69 (1H, br), 6.77 (1H, dd, J=2.2, 8.8 Hz), 6.91 (1H, d, J=2.2 Hz), 7.09-7.15 (1H, m), 7.31-7.40 (2H, m), 7.40-7.49 (2H, m), 7.49-7.60 (3H, m), 7.66-7.74 (1H, m), 8.06 (1H, br s).

Workup

  1. stirringby stirring at 50° C. for 24 hours
  2. waitThe reaction mixture was left
  3. temperatureto be cooled
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dba134f58b084b17aa127fe0378e624a
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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