Malononitrile → 2-[(4-Hydroxy-3-iodo-5-methoxyphenyl)methylene]propanedinitrile

HRID 727457Notes

Reaction equation

HRID 727457 reaction equation
[I:1][C:2]1[C:3]([OH:12])=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([CH:9]=1)[CH:7]=O.[C:13](#[N:17])[CH2:14][C:15]#[N:16]>N1CCCCC1.C(O)C>[CH3:11][O:10][C:4]1[CH:5]=[C:6]([CH:9]=[C:2]([I:1])[C:3]=1[OH:12])[CH:7]=[C:14]([C:13]#[N:17])[C:15]#[N:16]

Participants

5

Reactant 2

HCID 8010MalononitrileHCID 79499Benzaldehyde, 4-hydroxy-3-iodo-5-methoxy-

Product 1

HCID 521132-[(4-Hydroxy-3-iodo-5-methoxyphenyl)methylene]propanedinitrile

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

A preferred method of synthesis of (E)-1-cyano-3- (3-iodo-4,5-hydroxyphenyl)acrylonitrile (Compound 2) is as follows: The compound was prepared as described in Ohmichi et al., 1993, Biochemistry 32:4650 in two steps. First, 3-methoxy-4-hydroxy-5-iodobenzylidene malononitrile was prepared by adding 3 drops of piperidine to 1.4 g of 5-iodovanillin and 0.4 g of malononitrile in 25 ml of ethanol and refluxing the mixture for 4 hours. 0.8 g (49% yield) of a yellow solid resulted.

Workup

  1. customThe compound was prepared
  2. temperaturerefluxing the mixture for 4 hours

Sources & evidence

ORD record
ord-731894b144a04f6bbfeccc34ac5382c1
Source dataset
uspto-grants-1998_01
Patent number
US05712395

Reaction notes

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