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Water → n-[2-(2-Hydroxy-1,1-dimethylethyl)-6-nitro-1,2,3,4-tetrahydroquinolin-4-yl]-propionamide

HRID 1836311
ノート
印刷プレビュー

反応式

HRID 1836311 の反応式
[NH2:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[NH:5][CH:4]([C:15]([CH3:19])([CH3:18])[CH2:16][OH:17])[CH2:3]1.[C:20](Cl)(=[O:23])[CH2:21][CH3:22].O.C(OCC)(=O)C>N1C=CC=CC=1>[OH:17][CH2:16][C:15]([CH:4]1[CH2:3][CH:2]([NH:1][C:20](=[O:23])[CH2:21][CH3:22])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[NH:5]1)([CH3:19])[CH3:18]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 62324Propionyl chlorideHCID 234992302-(4-Amino-6-nitro-1,2,3,4-tetrahydroquinolin-2-yl)-2-methylpropan-1-ol

生成物 1

HCID 23499225n-[2-(2-Hydroxy-1,1-dimethylethyl)-6-nitro-1,2,3,4-tetrahydroquinolin-4-yl]-propionamide

試薬・触媒・溶媒 1

HCID 1049
Pyridine
溶媒

実験手順

The compound of Example 22 (50 mg) and 0.1 ml of propionyl chloride were dissolved in 1 ml of pyridine. After 2 hours of stirring at room temperature, water and ethyl acetate were added. The ethyl acetate layer was washed with water, and then dried over anhydrous sodium sulfate, followed by distilling off the solvent under reduced pressure. The residue was dissolved in 1 ml of methanol, 0.1 ml of a 4N aqueous solution of sodium hydroxide was added, and the mixture was stirred for 1 hour. Then, a phosphate buffer (pH 7.0) was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate) to obtain 31 mg of the title compound. Its physical properties are shown below.

後処理

  1. washThe ethyl acetate layer was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationby distilling off the solvent under reduced pressure
  4. dissolutionThe residue was dissolved in 1 ml of methanol
  5. addition0.1 ml of a 4N aqueous solution of sodium hydroxide was added
  6. stirringthe mixture was stirred for 1 hour
  7. additionThen, a phosphate buffer (pH 7.0) was added
  8. extractionthe mixture was extracted with ethyl acetate
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate)

出典と根拠

ORDレコード
ord-5b371854d3704920afc06597cd5ea4d9
出典データセット
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06777427B2

反応ノート

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