Potassium Hydroxide → HCID 15675283, compound

HRID 1090143Notes

Reaction equation

HRID 1090143 reaction equation
[C:1]([C:4]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[CH:7][C:5]=1[NH2:6])(=[O:3])[CH3:2].CN(C1C=CC=CN=1)C.[CH:24]1([C:27](Cl)=[O:28])[CH2:26][CH2:25]1.[OH-].[K+]>O1CCCC1.C(N(CC)CC)C>[CH:24]1([C:27]([NH:6][C:5]2[CH:7]=[C:8]([O:13][CH3:14])[C:9]([O:11][CH3:12])=[CH:10][C:4]=2[C:1](=[O:3])[CH3:2])=[O:28])[CH2:26][CH2:25]1

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 218852-DimethylaminopyridineHCID 77637Cyclopropanecarbonyl chlorideHCID 602085Ethanone, 1-(2-amino-4,5-dimethoxyphenyl)-

Product 1

HCID 15675283HCID 15675283, compoundYield 92.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

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. stirringthe mixture was stirred
  2. extractionextraction
  3. washThe extract was washed with saturated saline
  4. dry with materialdried over sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (Wako Gel C-200, 50 g)
  7. washElution with a mixed solvent of n-hexane (60 parts) and ethyl acetate (40 parts)

Sources & evidence

ORD record
ord-6f0ef6cf65d64eb485be16bf9882e820
Source dataset
uspto-grants-1992_01
Patent number
US05081121

Reaction notes

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