3-Morpholinophenol → 4-(3-(2-Nitropyridin-3-yloxy)phenyl)morpholine

HRID 335213

反応式

HRID 335213 の反応式
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].F[C:25]1[C:26]([N+:31]([O-:33])=[O:32])=[N:27][CH:28]=[CH:29][CH:30]=1>C1COCC1>[N+:31]([C:26]1[C:25]([O:13][C:9]2[CH:8]=[C:7]([N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)[CH:12]=[CH:11][CH:10]=2)=[CH:30][CH:29]=[CH:28][N:27]=1)([O-:33])=[O:32]

参加物

5

反応物 3

HCID 1413433-MorpholinophenolHCID 2724254Sodium bis(trimethylsilyl)amideHCID 27628023-Fluoro-2-nitropyridine

生成物 1

HCID 669951694-(3-(2-Nitropyridin-3-yloxy)phenyl)morpholine収率 73.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

In a 125 mL round-bottom flask, 3-morpholinophenol (0.91 g, 5.07 mmol) was dissolved in THF (40 mL). Solution was cooled to 0° C. and NaHMDS (5.07 mL, 5.07 mmol) (1M in THF) was added slowly. The mixture was agitated for 15 minutes and solution of 3-fluoro-2-nitropyridine (0.60 g, 4.22 mmol) in THF (5 mL) was added slowly. After agitating for 2 hours the solvent was evaporated and the residue dissolved in 100 mL of CH2Cl2 and washed with diluted sodium bicarbonate solution twice, dried over magnesium sulfate, filtered and evaporated. Crude material was purified by chromatography on silica gel, eluted with 25% ethyl acetate/Hexane to give the title compound (0.93 g, 72%) was obtained as thick red oil.

後処理

  1. stirringAfter agitating for 2 hours the solvent
  2. customwas evaporated
  3. dissolutionthe residue dissolved in 100 mL of CH2Cl2
  4. washwashed with diluted sodium bicarbonate solution twice
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customCrude material was purified by chromatography on silica gel
  9. washeluted with 25% ethyl acetate/Hexane

出典と根拠

ORDレコード
ord-00fe353d2b4d45f4b86eb8337e7e6ede
出典データセット
uspto-grants-2014_11
特許番号
US08883828B2

関連ノート

読み込み中…