HCID 15675283, compound → HCID 15675273, compound

HRID 1090144Notes

Reaction equation

HRID 1090144 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[CH:9][C:8]=2[C:17](=[O:19])[CH3:18])=O)[CH2:3][CH2:2]1.CC(C)([O-])C.[K+]>C(O)(C)(C)C>[CH:1]1([C:4]2[NH:6][C:7]3[C:8]([C:17](=[O:19])[CH:18]=2)=[CH:9][C:10]([O:15][CH3:16])=[C:11]([O:13][CH3:14])[CH:12]=3)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 15675283HCID 15675283, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 15675273HCID 15675273, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

2-Acetyl-4,5-dimethoxyaniline (2.0 g) was dissolved in tetrahydrofuran (50 ml), and to the mixture were added triethylamine (2.2 g) and dimethylaminopyridine (400 mg), and then a solution of cyclopropylcarbonyl chloride (1.7 g) in tetrahydrofuran (5 ml). The mixture was stirred at room temperature for 3 hours. After the addition of a 10% aqueous solution of potassium hydroxide, the mixture was stirred and extraction was conducted with chloroform. The extract was washed with saturated saline and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (Wako Gel C-200, 50 g). Elution with a mixed solvent of n-hexane (60 parts) and ethyl acetate (40 parts) gave N-cyclopropylcarbonyl-2-acetyl-4,5-dimethoxyaniline (2.5 g). This amide product (1.0 g) was suspended in t-butanol (50 ml), and potassium t-butoxide (2.1 g) was added to the suspension, and the mixture was heated under reflux for 15 hours. After the mixture was left to cool, extraction was conducted with a mixed solvent of chloroform (90 parts) and methanol (10 parts). The extract was washed with saturated saline and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (Wako Gel C-200, 30 g). Elution with a mixed solvent of chloroform (97 parts) and methanol (3 parts) gave 2-cyclopropyl-6,7dimethoxy-4(1H)-quinolone (compound 95, 580 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 hours
  3. waitAfter the mixture was left
  4. temperatureto cool
  5. extractionextraction
  6. washThe extract was washed with saturated saline
  7. dry with materialdried over sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (Wako Gel C-200, 30 g)
  10. washElution with a mixed solvent of chloroform (97 parts) and methanol (3 parts)

Sources & evidence

ORD record
ord-501ce3a69d2146889e84fd9b7de9f64c
Source dataset
uspto-grants-1992_01
Patent number
US05081121

Reaction notes

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