2-cyano-N,N-diethylacetamide → 2-Cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide

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.[CH2:14]([N:16]([CH2:22][CH3:23])[C:17](=[O:21])[CH2:18][C:19]#[N:20])[CH3:15]>>[CH2:14]([N:16]([CH2:22][CH3:23])[C:17](=[O:21])[C:18]([C:19]#[N:20])=[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)[CH3:15]

Participants

Reactant 2

HCID 38545152-cyano-N,N-diethylacetamide

HCID 57489573,4-Dihydroxy-5-nitrobenzaldehyde

Product 1

HCID 46595682-Cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide

Procedure

The procedure described in Example 99 was repeated using 1.83 g of 3,4-dihydroxy-5-nitrobenzaldehyde and 1.5 g of N,N-diethylcyanoacetamide. Yield 2.23 g (73%), m.p. 153°-156° C.

Sources & evidence

ORD record: ord-182788c139d84eaa8dee7a82817b63f6
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05283352

Reaction notes

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