Malononitrile → HCID 2839615, compound

HRID 392384Notes

Reaction equation

HRID 392384 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[C:11](#[N:15])[CH2:12][C:13]#[N:14].[CH3:16][C:17]1([CH3:25])[CH2:22][C:21](=[O:23])[CH2:20][C:19](=[O:24])[CH2:18]1>CCO.N1CCCCC1>[NH2:14][C:13]1[O:24][C:19]2[CH2:18][C:17]([CH3:25])([CH3:16])[CH2:22][C:21](=[O:23])[C:20]=2[CH:1]([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)[C:12]=1[C:11]#[N:15]

Participants

6

Reactant 3

HCID 8010MalononitrileHCID 312444-MethoxybenzaldehydeHCID 31358Dimedone

Product 1

HCID 2839615HCID 2839615, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

A stirred solution of p-anisaldehyde (1.74 mL, 14.3 mmol) and malononitrile (0.90 mL, 14.28 mmol) in 75 mL of 95% EtOH at RT was treated with a few drops of piperidine and after about 5 min, a yellow precipitate was formed and the mixture was stirred for another 10 min after which 5,5-dimethylcyclohexan-1,3-dione (2.00 g, 14.3 mmol) was added as a solid in one portion. The stirred suspension became a solution after about 5 min. After about 2 h a white precipitate was formed and TLC analysis showed complete reaction. The precipitate was filtered and washed with cold 95% EtOH then dried under vacuum, resulting in 3.71 g (81%) of the title compound as a white solid, mp 197-200° C. 1H NMR (DMSO-d6): 7.04 (d, 2H), 6.96 (bs, 2H), 6.83 (d, 2H), 4.11 (s, 1H), 3.71 (s, 3H), 2.49 (m, 2H), 2.15 (m, 2H), 1.03 (s, 3H), 0.94 (s, 3H).

Workup

  1. customa yellow precipitate was formed
  2. additionwas added as a solid in one portion
  3. customafter about 5 min
  4. customAfter about 2 h a white precipitate was formed
  5. customreaction
  6. filtrationThe precipitate was filtered
  7. washwashed with cold 95% EtOH
  8. customthen dried under vacuum

Sources & evidence

ORD record
ord-b70914d1609e416896b135257ded1599
Source dataset
uspto-grants-2004_10
Patent number
US06800657B2

Reaction notes

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