Diethyl (ethoxymethylene)malonate → HCID 15675229, compound

HRID 1090119Notes

Reaction equation

HRID 1090119 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([O:10][CH2:11][O:12][CH3:13])=[C:7]([CH:9]=1)[NH2:8].C([O:16][CH:17]=[C:18]([C:24](OCC)=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20])C>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:22]([O:21][C:19]([C:18]1[C:17](=[O:16])[C:9]2[C:7](=[C:6]([O:10][CH2:11][O:12][CH3:13])[CH:5]=[CH:4][C:3]=2[O:2][CH3:1])[NH:8][CH:24]=1)=[O:20])[CH3:23]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 15675228HCID 15675228, compound

Product 1

HCID 15675229HCID 15675229, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

5-Methoxy-2-methoxymethoxyaniline (3.6 g) and diethyl ethoxymethylenemalonate (4.5 g) were heated at a temperature of 100°-120° C. for 1 hour. Eighty milliliter of diphenyl ether was added to the mixture, and the resulting mixture was further heated at 250°-260° C. for 1.5 hours. After the mixture was left to cool down to room temperature, it was purified by silica gel column chromatography (Wako Gel C-200, 140 g). Elution with a mixed solvent of chloroform (97 parts) and methanol (3 parts) gave 3.0 g of 3-ethoxycarbonyl-5-methoxy-8-methoxymethoxy-4(1H)-quinolone (compound 5).

Workup

  1. temperaturethe resulting mixture was further heated at 250°-260° C. for 1.5 hours
  2. waitAfter the mixture was left
  3. customit was purified by silica gel column chromatography (Wako Gel C-200, 140 g)
  4. washElution with a mixed solvent of chloroform (97 parts) and methanol (3 parts)

Sources & evidence

ORD record
ord-729291d3957341aaa2fa747c67d91229
Source dataset
uspto-grants-1992_01
Patent number
US05081121

Reaction notes

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