Diethyl (ethoxymethylene)malonate → HCID 12733848, compound

HRID 544233Notes

Reaction equation

HRID 544233 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[Cl:9].CC[O:12][CH:13]=[C:14]([C:20](OCC)=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16]>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:18]([O:17][C:15]([C:14]1[C:13](=[O:12])[C:7]2[C:5](=[CH:4][C:3]([Cl:9])=[C:2]([Br:1])[CH:8]=2)[NH:6][CH:20]=1)=[O:16])[CH3:19]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 888884-Bromo-3-chloroaniline

Product 1

HCID 12733848HCID 12733848, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

A mixture of 4-bromo-3-chloroaniline (8.3 g) and diethyl ethoxymethylene malonate (8.9 g) was heated at 120°-130° C. for 1.5 hours. The mixture was added to diphenyl ether (140 ml) and refluxed for 30 minutes. The cooled mixture was filtered, the solid was washed with benzene and dried. The solid was recrystallized from DMF to give 6-bromo-7-chloro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid ethyl ester (11.7 g).

Workup

  1. temperaturewas heated at 120°-130° C. for 1.5 hours
  2. temperaturerefluxed for 30 minutes
  3. filtrationThe cooled mixture was filtered
  4. washthe solid was washed with benzene
  5. customdried
  6. customThe solid was recrystallized from DMF

Sources & evidence

ORD record
ord-4afc6152d52f426296febbc6db755c00
Source dataset
uspto-grants-1984_05
Patent number
US04448962

Reaction notes

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