Diethyl (ethoxymethylene)malonate → Diethyl 2-((2-nitrophenylamino)methylene)malonate

HRID 1531683Notes

Reaction equation

HRID 1531683 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].C(O[CH:14]=[C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])C>C(O)C>[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH:6][CH:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:21]([O:23][CH2:24][CH3:25])=[O:22])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 69462-Nitroaniline

Product 1

HCID 225911Diethyl 2-((2-nitrophenylamino)methylene)malonateYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-nitroaniline (41.4 g) and diethyl ethoxymethylenemalonate (66 ml) was heated on a steam bath for 24 hours. The hot reaction mixture was treated with ethanol (300 ml), cooled and filtered to give diethyl (2-nitroanilino)methylenemalonate in 88% yield, mp 104-105° C.

Workup

  1. temperaturewas heated on a steam bath for 24 hours
  2. temperaturecooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-e08daf3ae6034b70bbdfa44d4182e235
Source dataset
uspto-grants-2001_03
Patent number
US06200974B1

Reaction notes

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