Dichloromethane → (Z)-3-(3-nitro-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile

HRID 260096

Reaction equation

HRID 260096 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH:7]=O)([O-:3])=[O:2].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH2:26][C:27]#[N:28])[CH:19]=[C:20]([O:24][CH3:25])[C:21]=1[O:22][CH3:23].[OH-].[Na+].ClCCl>O.[Cl-].C([NH2+]C)CCCCCCC>[N+:1]([C:4]1[CH:5]=[C:6](/[CH:7]=[C:26](/[C:18]2[CH:19]=[C:20]([O:24][CH3:25])[C:21]([O:22][CH3:23])=[C:16]([O:15][CH3:14])[CH:17]=2)\[C:27]#[N:28])[CH:9]=[CH:10][C:11]=1[O:12][CH3:13])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 258873,4,5-TrimethoxyphenylacetonitrileHCID 7006084-Methoxy-3-nitrobenzaldehyde

Product 1

HCID 10619131(Z)-3-(3-nitro-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrileYield 72.4%

Reagents, catalysts & solvents 2

HCID 22561414N-Methyloctan-1-amine--hydrogen chloride (1/1)CatalystHCID 962WaterSolvent

Procedure

3.0 g of 3-nitro-4-methoxybenzaldehyde, 3.4 g of 3,4,5-trimethoxyphenylacetonitrile, 800 mg of sodium hydroxide and 100 mg of octylmethylammonium chloride were dissolved in 15 ml of water and 15 ml of dichloromethane and reacted for 4 hours at room temperature. Ice water was added to the reaction liquid, which was then extracted three times each with dichloromethane. The extract was dried with anhydrous sodium sulfate and concentrated. The concentrated liquid was purified by crystallization (ethyl acetate) to obtain 4.4 g of the intended compound. The yield was 72%.

Workup

  1. extractionwas then extracted three times each with dichloromethane
  2. dry with materialThe extract was dried with anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe concentrated liquid was purified by crystallization (ethyl acetate)

Sources & evidence

ORD record
ord-1fc0a5e64cea4a7692a615b3c55a2b09
Source dataset
uspto-grants-1996_06
Patent number
US05525632

Linked notes

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