Iodoethane → HCID 86745379, compound

HRID 1090137Notes

Reaction equation

HRID 1090137 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[NH2:5].C(O[CH:14]=[C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])C.C(=O)([O-])[O-].[K+].[K+].[CH2:32](I)[CH3:33]>CN(C)C=O>[CH2:32]([O:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[NH:5][CH:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH3:33]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 6871Diethyl (ethoxymethylene)malonateHCID 11430Potassium CarbonateHCID 743145-Amino-2-methoxyphenol

Product 1

HCID 86745379HCID 86745379, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Hydroxy-4-methoxyaniline (0.64 g) and diethyl ethoxymethylenemalonate (1.20 g) were stirred at 115° for 30 minutes. Dimethylformamide (9.6 ml), potassium carbonate (960 mg) and ethyl iodide (0.44 ml) were added to the mixture, and the whole mixture was stirred at room temperature for 20 hours. The precipitate was removed by filtration, and the filtrate was concentrated and purified by silica gel column chromatography (Wako Gel C-200, 25 g) to give diethyl (3-ethoxy-4-methoxyanilino)methylenemalonate (1.5 g). The product was suspended in diphenyl ether (19.5 ml), and the suspension was stirred at 250°-260° for 6 hours. After the reaction mixture was left to cool down to room temperature, ether was added to the mixture and the precipitate was collected by filtration. It was purified by silica gel column chromatography (Wako Gel C-200, 35 g) to give 7-ethoxy-6-methoxy-4(1H)-quinolone (compound 62, 280 mg).

Workup

  1. customThe precipitate was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. custompurified by silica gel column chromatography (Wako Gel C-200, 25 g)

Sources & evidence

ORD record
ord-557104373c6b4434a0fea3c02dbb2dd3
Source dataset
uspto-grants-1992_01
Patent number
US05081121

Reaction notes

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