Ethyl cyanoacetate → 6,7-Dihydroxy-2-imino-2H-chromene-3-carboxylic acid ethyl ester

HRID 965783Notes

Reaction equation

HRID 965783 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[C:7]([OH:11])=[CH:6][C:3]=1[CH:4]=O.[C:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:13]>CN(C=O)C.N1CCCCC1.C(O)(=O)C>[CH2:18]([O:17][C:15]([C:14]1[C:12](=[NH:13])[O:1][C:2]2[C:3]([CH:4]=1)=[CH:6][C:7]([OH:11])=[C:8]([OH:10])[CH:9]=2)=[O:16])[CH3:19]

Participants

6

Reactant 2

HCID 7764Ethyl cyanoacetateHCID 6433872,4,5-Trihydroxybenzaldehyde

Product 1

HCID 1363776256,7-Dihydroxy-2-imino-2H-chromene-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,4,5-trihydroxybenzaldehyde (2.94 g) and ethyl cyanoacetate (1.62 g) in DMF (20 ml) were added 20 drops (Pasteur pipette) of piperidine and eight drops of acetic acid and the solution kept at 80° C. under nitrogen for two hours. The product was filtered and washed with DMF and ethyl ether. Yield: 2.00 g.

Workup

  1. filtrationThe product was filtered
  2. washwashed with DMF and ethyl ether

Sources & evidence

ORD record
ord-3c8480c2150a4cc39986f0d6baa4f641
Source dataset
uspto-grants-2005_10
Patent number
US06951870B2

Reaction notes

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