Water → HCID 53412265, compound

HRID 973444Notes

Reaction equation

HRID 973444 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=O.[C:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:12].O>C(O)C.N1CCCCC1>[C:11]([C:13](=[CH:5][C:4]1[CH:7]=[CH:8][C:9]([OH:10])=[C:2]([OH:1])[CH:3]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:12]

Participants

6

Reactant 3

HCID 962WaterHCID 7764Ethyl cyanoacetateHCID 87683,4-Dihydroxybenzaldehyde

Product 1

HCID 53412265HCID 53412265, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3,4-dihydroxybenzaldehyde (2.0 g, 14.5 mmol) in ethanol (10 ml) were added ethyl cyanoacetate (1.6 g, 14.5 mmol) and piperidine (3 drops) and the resulting reaction was allowed to proceed for 20 hours at room temperature. Water was then added to the reaction mixture, and the precipitated crystalline was filtered off and recrystallized from ethanol-water to yield the titled compound (2.3 g, 9.9 mmol). Alternatively, the reaction may be conducted in a benzene solution under refluxing conditions. Compound Nos. 2 to 6 were provided in a similar manner.

Workup

  1. customthe resulting reaction
  2. filtrationthe precipitated crystalline was filtered off
  3. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-2c268e55253b45b7a643ee41b348c1c5
Source dataset
uspto-grants-1991_11
Patent number
US05063243

Reaction notes

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