Diethyl Malonate → HCID 19592542, compound

HRID 613458Notes

Reaction equation

HRID 613458 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].CC(C)([O-])C.[K+].[Br:18][C:19]1[CH:20]=[N:21][C:22]2[C:27]([C:28]=1Cl)=[CH:26][CH:25]=[CH:24][C:23]=2[N+:30]([O-:32])=[O:31].[Cl-].[NH4+]>CN1CCCC1=O>[CH2:10]([O:9][C:1]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:28]1[C:27]2[C:22](=[C:23]([N+:30]([O-:32])=[O:31])[CH:24]=[CH:25][CH:26]=2)[N:21]=[CH:20][C:19]=1[Br:18])=[O:8])[CH3:11]

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 25517Ammonium ChlorideHCID 19592814HCID 19592814, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19592542HCID 19592542, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a mixture of diethyl malonate (368 mg) and N-methylpyrrolidone was added potassium tert-butoxide (246 mg) at 0° C., and the mixture was stirred for 30 minutes at ambient temperature. To a mixture was added 3-bromo-4-chloro-8-nitroquinoline (300 mg), and the mixture was stirred for 30 minutes at ambient temperature and for 30 minutes at 50° C. The mixture was poured into saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo to give 4-[bis(ethoxycarbonyl)methyl]-3-bromo-8-nitroquinoline (315.6 mg).

Workup

  1. stirringthe mixture was stirred for 30 minutes at ambient temperature and for 30 minutes at 50° C
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-306d4712171440a79897f9468c78e964
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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