Acetic Acid → Ethyl 2-chloro-5-nitro-alpha-cyanocinnamate

HRID 2254906Notes

Reaction equation

HRID 2254906 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[Cl:9][C:10]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:11]=1[CH:12]=O.N1CCCCC1.C(O)(=O)C>O1CCCC1>[Cl:9][C:10]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:11]=1[CH:12]=[C:3]([C:1]#[N:2])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 729332-Chloro-5-nitrobenzaldehyde

Product 1

HCID 314268Ethyl 2-chloro-5-nitro-alpha-cyanocinnamateYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

29.7 g (300 millimoles) of ethyl cyanoacetate were added to a solution of 55.7 g (300 millimoles) of 2-chloro-5-nitrobenzaldehyde in 200 ml of tetrahydrofuran, after which 1 ml of piperidine was added as a catalyst at 0° C. The mixture was stirred for 16 hours at room temperature, neutralized with acetic acid and then worked up in a conventional manner to give a product of melting point 83°-85° C. in 71% yield.

Workup

  1. customto give a product of melting point 83°-85° C. in 71% yield

Sources & evidence

ORD record
ord-f7127dd1a80f4f18833d44d564cf7778
Source dataset
uspto-grants-1993_08
Patent number
US05237089

Reaction notes

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