Diethyl (ethoxymethylene)malonate → HCID 15675226, compound

HRID 1090118Notes

Reaction equation

HRID 1090118 reaction equation
C([O:8][C:9]1[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][C:10]=1[NH2:11])C1C=CC=CC=1.C([O:20][CH:21]=[C:22]([C:28](OCC)=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24])C>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:26]([O:25][C:23]([C:22]1[C:21](=[O:20])[C:12]2[C:10](=[C:9]([OH:8])[C:15]([O:16][CH3:17])=[CH:14][CH:13]=2)[NH:11][CH:28]=1)=[O:24])[CH3:27]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 13596187HCID 13596187, compound

Product 1

HCID 15675226HCID 15675226, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

Two grams of 2-benzyloxy-3-methoxyaniline and 2.3 g of diethyl ethoxymethylenemalonate were heated at a temperature of 100°-120° C. for 1 hour. Fifty milliliter of diphenyl ether was added to the mixture, and the resulting mixture was further heated at 250°-270° C. for 1.5 hours. After the mixture was cooled down to room temperature, it was purified by silica gel column chromatography (Wako Gel C-200, 100 g). Elution with a mixed solvent of chloroform (95 parts) and methanol (5 parts) gave 980 mg of 3-ethoxycarbonyl-8-hydroxy-7-methoxy-4(1H)-quinolone.

Workup

  1. temperaturethe resulting mixture was further heated at 250°-270° C. for 1.5 hours
  2. customit was purified by silica gel column chromatography (Wako Gel C-200, 100 g)
  3. washElution with a mixed solvent of chloroform (95 parts) and methanol (5 parts)

Sources & evidence

ORD record
ord-ef8294e4d00340069049079b77a40ccc
Source dataset
uspto-grants-1992_01
Patent number
US05081121

Reaction notes

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