2-Nitrobenzaldehyde → HCID 41281, compound

HRID 1687578Notes

Reaction equation

HRID 1687578 reaction equation
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[N+:14]([C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=O)([O-:16])=[O:15].[Cl-].[NH4+]>CN(C=O)C>[N+:14]([C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=[CH:5][C:3]#[N:4])([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 111012-NitrobenzaldehydeHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 75676Diethyl (cyanomethyl)phosphonate

Product 1

HCID 41281HCID 41281, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride, 60% disp. in mineral oil (0.265 g) was added in portions to a solution of Diethyl cyanomethylphosphonate (1.17 g, 6.6 mmol) in anhydrous DMF (20 mL, 0.2 mol) under stirring and ice cooling. A solution of 2-Nitrobenzaldehyde (1.00 g, 6.6 mmol) in DMF (5 mL) was then added dropwise over 10 min. After being stirred for 5 min, the reaction mixture was poured into ice water, neutralized with ammonium chloride, and extracted with ether. The organic solution was dried over MgSO4, filtered, and concentrated under reduced pressure. A mixture of E and Z 3-(2-Nitro-phenyl)-acrylonitrile was isolated (892 mg, combined yield=77%.)

Workup

  1. stirringAfter being stirred for 5 min
  2. extractionextracted with ether
  3. dry with materialThe organic solution was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. additionA mixture of E

Sources & evidence

ORD record
ord-931cc7739363474294e1a1253ec015e3
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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