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Sodium Iodide → 5-Methoxy-4-[3-(morpholin-4-yl)propyloxy]-2-nitrobenzaldehyde

HRID 1821425
ノート
印刷プレビュー

反応式

HRID 1821425 の反応式
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:13]([O:14][CH3:15])=[CH:12][C:9]([CH:10]=[O:11])=[C:8]([N+:16]([O-:18])=[O:17])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.[I-].[Na+]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:15][O:14][C:13]1[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[CH:7][C:8]([N+:16]([O-:18])=[O:17])=[C:9]([CH:12]=1)[CH:10]=[O:11]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 5238Sodium IodideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 866282194-(3-Chloropropyloxy)-5-methoxy-2-nitrobenzaldehyde

生成物 1

HCID 866282185-Methoxy-4-[3-(morpholin-4-yl)propyloxy]-2-nitrobenzaldehyde収率 54%

試薬・触媒・溶媒 3

HCID 74236
Tetrabutylammonium Bromide
触媒
HCID 962Water溶媒2 回
HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

4-(3-Chloropropyloxy)-5-methoxy-2-nitrobenzaldehyde (0.40 g, 1.5 mmol) was dissolved in toluene (6.0 mL) and the solution was added with potassium carbonate (1.0 g, 7.3 mmol) dissolved in morpholine (0.38 mL, 4.4 mmol), sodium iodide (0.44 g, 2.9 mmol), tetrabutylammonium bromide (24 mg, 0.007 mmol) and water (2.0 mL), followed by stirring at 100° C. for 19 hours. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The filtrate was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 to 0/100) and concentrated to obtain 5-methoxy-4-[3-(morpholin-4-yl)propyloxy]-2-nitrobenzaldehyde (0.26 g, 54%).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe filtrate was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 to 0/100)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-85a5bf4bc6f04f29b8200ec1b4f667b3
出典データセット
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07605272B2

反応ノート

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