Hydrochloric Acid → HCID 71253087, compound

HRID 571096Notes

Reaction equation

HRID 571096 reaction equation
[CH3:1][C:2]([CH3:9])([CH3:8])[C:3](=O)[CH2:4][C:5]#[N:6].Cl.Cl.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([NH:22][NH2:23])[CH:17]=[C:18]([O:20][CH3:21])[CH:19]=1>CCO.C([O-])(O)=O.[Na+]>[C:2]([C:3]1[CH:4]=[C:5]([NH2:6])[N:22]([C:16]2[CH:17]=[C:18]([O:20][CH3:21])[CH:19]=[C:14]([O:13][CH3:12])[CH:15]=2)[N:23]=1)([CH3:9])([CH3:8])[CH3:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 67451229(3,5-dimethoxyphenyl)hydrazine hydrochloride

Product 1

HCID 71253087HCID 71253087, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 4,4-dimethyl-3-oxopentanenitrile (754 mg, 6.02 mmol) and conc hydrochloric acid (12 M, 500 μL, 6.0 mmol) in EtOH (25 mL) was added 3,5-dimethoxyphenylhydrazine hydrochloride (1.12 g, 5.47 mmol) and the reaction mixture heated at reflux for 1 hr and then cooled to RT. After 23 hr the reaction mixture was diluted with saturated aq. NaHCO3 (50 mL) then extracted with DCM (4×50 mL). The combined organic extracts were dried and evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, 40 g, EtOAc in isohexane, 0-100%, gradient elution) and then by SCX capture and release to afford the title compound, Intermediate A25, as a dark orange solid (400 mg, 26%); Rt 1.70 min (Method 2); m/z 276 (M+H)+, (ES+).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 1 hr
  3. extractionthen extracted with DCM (4×50 mL)
  4. customThe combined organic extracts were dried
  5. customevaporated in vacuo
  6. customthe residue was purified by flash column chromatography (SiO2, 40 g, EtOAc in isohexane, 0-100%, gradient elution)

Sources & evidence

ORD record
ord-26e51276c6294f5291c668528f77717a
Source dataset
uspto-grants-2015_05
Patent number
US09024041B2

Reaction notes

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