Diethyl (ethoxymethylene)malonate → HCID 20207465, compound

HRID 542896Notes

Reaction equation

HRID 542896 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([OH:9])[CH:8]=1)[NH2:5].C(O[CH:13]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])C>C(O)C>[CH2:23]([O:22][C:20]([C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][NH:5][C:4]1[CH:3]=[C:2]([OH:1])[CH:8]=[C:7]([OH:9])[CH:6]=1)=[O:21])[CH3:24]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 4107515-Aminobenzene-1,3-diol

Product 1

HCID 20207465HCID 20207465, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3,5-dihydroxyaniline (2.0 g), 2-ethoxy-1,1-bis(ethoxycarbonyl)ethene (3.0 g) and ethanol (10 ml) was left to stand at room temperature for 2 days. The resulting solid was filtered off, dissolved in dimethylsulphoxide (20 ml) and then treated with water (100 ml). The resulting solid was washed with water, to give 1,1-bis(ethoxycarbonyl)-2-(3,5-dihydroxyphenylamino)ethene (3.2 g), m.p. 190°-192° C.

Workup

  1. waitwas left
  2. filtrationThe resulting solid was filtered off
  3. dissolutiondissolved in dimethylsulphoxide (20 ml)
  4. additiontreated with water (100 ml)
  5. washThe resulting solid was washed with water

Sources & evidence

ORD record
ord-f87a7a8ee59749e1b4a6fac1317f8799
Source dataset
uspto-grants-1987_04
Patent number
US04659727

Reaction notes

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