O-Cresol → HCID 89812984, compound

HRID 1481190Notes

Reaction equation

HRID 1481190 reaction equation
[N+]([C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=1)[C:8]#[N:9])([O-])=O.[C:14]1([CH3:21])[C:19]([OH:20])=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[C:14]1([CH3:21])[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=1[O:20][C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=1)[C:8]#[N:9]

Participants

6

Reactant 4

HCID 335O-CresolHCID 962WaterHCID 11430Potassium CarbonateHCID 974431,2-Benzenedicarbonitrile, 4-nitro-

Product 1

HCID 89812984HCID 89812984, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-nitrophthalonitrile (10.6 g, 60.0 mmol), o-cresol (7.9 g, 72.0 mmol) and K2CO3 (16.6 g, 120.0 mmol) in DMF (70 mL) was heated to 60° C. under a nitrogen atmosphere for 3 hours. The crude reaction was then poured into H2O (300 mL). The resulting mixture was extracted twice with EtOAc. The combined organic layers were washed with sat'd NaHCO3 solution, dried over MgSO4 and concentrated in vacuo. The residue was then dissolved in EtOH (60 mL). After storing for 5 hours at room temperature, the precipitate was collected by filtration and the filter cake was washed with cold EtOH to give the title compound in 8.9 g. MS: (+) m/z 235.46 (M+1).

Workup

  1. customThe crude reaction
  2. extractionThe resulting mixture was extracted twice with EtOAc
  3. washThe combined organic layers were washed with sat'd NaHCO3 solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was then dissolved in EtOH (60 mL)
  7. filtrationthe precipitate was collected by filtration
  8. washthe filter cake was washed with cold EtOH

Sources & evidence

ORD record
ord-4447f751443c49139c164537ee0ccf21
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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