Acrylonitrile → HCID 68838102, compound

HRID 490561Notes

Reaction equation

HRID 490561 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][NH:8][C:7]2=[O:13])([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].[C:20](#[N:23])[CH:21]=[CH2:22]>O>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:22][CH2:21][C:20]#[N:23])[NH:8][C:7]2=[O:13])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 11430Potassium CarbonateHCID 53746612,3-Dihydro-5-nitro-1H-indazol-3-one

Product 1

HCID 68838102HCID 68838102, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

5-Nitro-1,2-dihydro-indazol-3-one (prepared according to Org. Synth. 1949, 29, 54 or Chem Ber. 1942, 75, 1104) (0.6 g) was suspended in water (8 mL) and 2N K2CO3 (aq.) (1.8 g) was added to the flask and the mixture was heated to 50° C. for 10 minutes. Acrylonitrile (0.24 mL) was then added dropwise. The reaction was stirred overnight and was quenched with 2 N HCl (aq.) solution while cooling in an ice bath. The aqueous phase was extracted with EtOAc and the combined phases were washed with brine, dried over sodium sulfate, filtered and reduced in vacuo. Flash column chromatography over silica gel (eluting with EtOAc, nheptane, 3% AcOH) afforded pure desired 3-(5-Nitro-3-oxo-2,3-dihydro-indazol-1-yl)-propionitrile as a white solid. MS (ESI+: 233.3[M+H]+).

Workup

  1. customwas quenched with 2 N HCl (aq.) solution
  2. temperaturewhile cooling in an ice bath
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washthe combined phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-6bfc72e327694d3bb79465eb32f927e9
Source dataset
uspto-grants-2009_05
Patent number
US07528158B2

Reaction notes

Loading…