Malononitrile → HCID 86177505, compound

HRID 487252Notes

Reaction equation

HRID 487252 reaction equation
[H-].[Na+].[C:3](#[N:7])[CH2:4][C:5]#[N:6].[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH2:18][C:19](Cl)=[O:20])[CH:13]=[CH:14][C:15]=1[O:16][CH3:17]>C1COCC1>[OH:20][C:19](=[C:4]([C:3]#[N:7])[C:5]#[N:6])[CH2:18][C:12]1[CH:13]=[CH:14][C:15]([O:16][CH3:17])=[C:10]([O:9][CH3:8])[CH:11]=1

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 24758Sodium hydrideHCID 3604458(3,4-Dimethoxyphenyl)acetyl chloride

Product 1

HCID 86177505HCID 86177505, compoundYield 110.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 60% NaH/mineral oil dispersion (6.0 g, 0.15 moles) in THF (230 ml) in an ice-bath was added dropwise malononitrile (9.9 g, 0.15 mol). The reaction mixture was stirred for 2 hours at 0° C. and 3,4-dimethoxyphenyl acetylchloride (32.2 g, 0.15 mol) in THF (50 ml) was added dropwise over 2 hours. The reaction mixture was warmed to room temperature and stirred for 24 hours. The solvent was removed in vacuo, and the residue was partitioned between chloroform and 2N H2SO4. The organic layer was separated and the aqueous layer was extracted with chloroform (2×150 ml). The organic layers were combined and the solvent was removed in vacuo to afford 40.4 g (crude) of (1-hydroxy-(3,4-dimethoxyphenylethylidene))malononitrile as a brown oil, which was used directly in the following reaction without purification.

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. stirringstirred for 24 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between chloroform and 2N H2SO4
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with chloroform (2×150 ml)
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-7de8598f64ff4b74b676c0afa35890e1
Source dataset
uspto-grants-1994_03
Patent number
US05294612

Reaction notes

Loading…