2-Cyano-N,N-dimethylacetamide → N,N-Dimethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide

HRID 1088884Notes

Reaction equation

HRID 1088884 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[OH:10])[CH:5]=O.[CH3:14][N:15]([CH3:21])[C:16](=[O:20])[CH2:17][C:18]#[N:19].C(O)(=O)C.N1CCCCC1>C(O)C>[CH3:14][N:15]([CH3:21])[C:16](=[O:20])[C:17]([C:18]#[N:19])=[CH:5][C:4]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]([OH:10])=[C:2]([OH:1])[CH:3]=1

Participants

5

Reactant 3

HCID 2511432-Cyano-N,N-dimethylacetamideHCID 57489573,4-Dihydroxy-5-nitrobenzaldehydeHCID 9793820Piperidine, acetate

Product 1

HCID 54424215N,N-Dimethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution containing 1.83 g of 3,4-dihydroxy-5-nitrobenzaldehyde, 1.2 g of N,N-dimethylcyanoacetamide and catalytic amount of piperidine acetate in 40 ml of dry ethanol was refluxed over night. Yield 1.1 g (40%), m.p. 183°-185° C.

Workup

  1. temperaturewas refluxed over night

Sources & evidence

ORD record
ord-95e05ae9ecba4669a6b0dd9e009632f8
Source dataset
uspto-grants-1990_10
Patent number
US04963590

Reaction notes

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