Water → 4-(4-Methylpyridin-2-yl)-2-nitrocinnamonitrile

HRID 1060008Notes

Reaction equation

HRID 1060008 reaction equation
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[CH3:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([C:21]2[CH:28]=[CH:27][C:24]([CH:25]=O)=[C:23]([N+:29]([O-:31])=[O:30])[CH:22]=2)[CH:16]=1.O>O1CCCC1>[CH3:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([C:21]2[CH:28]=[CH:27][C:24]([CH:25]=[CH:5][C:3]#[N:4])=[C:23]([N+:29]([O-:31])=[O:30])[CH:22]=2)[CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 186675944-(4-Methylpyridin-2-yl)-2-nitrobenzaldehyde

Product 1

HCID 545662564-(4-Methylpyridin-2-yl)-2-nitrocinnamonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (60% dispersion in mineral oil, 240 mg) in tetrahydrofuran (10 ml) was added a solution of diethyl cyanomethylphosphonate (0.971 ml) dropwise at 0° C., and the mixture was stirred at ambient temperature for 30 minutes. Then to the resultant mixture was added a solution of 4-(4-methylpyridin-2-yl)-2-nitrobenzaldehyde (1.21 g) in tetrahydrofuran (15 ml) dropwise at 0° C., and the mixture was stirred at ambient temperature for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was triturated with diisopropyl ether, filtered and dried to give 4-(4-methylpyridin-2-yl)-2-nitrocinnamonitrile (1.22 g) as a mixture of regioisomers.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was triturated with diisopropyl ether
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-bc78b00214d2433086d2819e521cfe2d
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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