Benzonitrile → HCID 178515310, compound

HRID 588267Notes

Reaction equation

HRID 588267 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11]([NH:13][NH2:14])=O)[CH:8]=2)[NH:3]1.[C:15](#[N:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].C(Cl)(Cl)Cl.CO>CCCCO.CN(C=O)C>[C:16]1([C:15]2[N:22]=[C:11]([C:7]3[CH:8]=[C:9]4[C:4](=[CH:5][CH:6]=3)[NH:3][C:2](=[O:1])[CH2:10]4)[NH:13][N:14]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 7505BenzonitrileHCID 11430Potassium CarbonateHCID 21584188Chloroform methanolHCID 904183972-Oxoindoline-5-carbohydrazide

Product 1

HCID 178515310HCID 178515310, compoundYield 5.2%

Reagents, catalysts & solvents 1

HCID 86623466DMF n-butanolSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 2-oxoindoline-5-carbohydrazide (200 mg, 1.05 mmol) in n-BuOH/DMF (6 ml/2 ml) was added benzonitrile (324 mg, 3.14 mmol) and potassium carbonate (29 mg, 0.21 mmol). The mixture was heated at 150° C. for 3 hours under microwave irradiation. CHCl3/MeOH (20 ml/1 ml) was added to the mixture and insoluble solid was removed by filtration. The filtrate was concentrated. H2O was added to the residue and extracted with CHCl3. The organic layer was dried over Na2SO4 and concentrated in vacuo. Purification by column chromatography (CHCl3/MeOH) gave 5-(3-phenyl-1H-1,2,4-triazol-5-yl)indolin-2-one (15 mg).

Workup

  1. customwas removed by filtration
  2. concentrationThe filtrate was concentrated
  3. additionH2O was added to the residue
  4. extractionextracted with CHCl3
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-faedffe33e6a485ba86dd6efbe965ec6
Source dataset
uspto-grants-2016_01
Patent number
US09227962B2

Reaction notes

Loading…