Water → 2-Fluoro-6-[(2-methoxyethyl)amino]benzonitrile

HRID 897589ノート

反応式

HRID 897589 の反応式
F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[C:4]#[N:5].COC[CH2:14][CH2:15][NH2:16].[C:17](=[O:20])([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([NH:16][CH2:15][CH2:14][O:20][CH3:17])[C:3]=1[C:4]#[N:5]

参加物

6

反応物 4

HCID 962WaterHCID 16723-MethoxypropylamineHCID 11430Potassium CarbonateHCID 746952,6-Difluorobenzonitrile

生成物 1

HCID 223466972-Fluoro-6-[(2-methoxyethyl)amino]benzonitrile収率 71.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 2,6 difluorobenzonitrile (3.5 g, 25.16 mmol) in dimethylformamide (50 mL) was treated with 3-methoxypropylamine (2.24 g, 25.16 mmol) and potassium carbonate (6.94 g, 50.32 mmol). The reaction mixture was stirred over night under a nitrogen atmosphere. Water (100 mL) was added to the reaction solution. The layers were partitioned, and the aqueous layer was extracted with ethyl acetate (1.2 L). The combined organic layers were washed with water (1.5 L), dried over magnesium sulfate, filtered, and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel using 7:1 heptane:ethyl acetate as the eluent. The column afforded 3.5 g (68%) of 2-fluoro-6-[(2-methoxyethyl)amino]benzonitrile. 1H NMR (DMSO-d6, 400 MHz) δ 7.48-7.39 (m, 1H), 6.64-6.48 (m, 2H), 3.45-3.31 (m, 2H), 3.30-3.20 (m, 5H), 1.85-1.75 (m, 2H); HPLC Waters 2690 Alliance HPLC (Symmetry Shield RP18 3.5 μm, 2.1×50 mm; 5%-95% acetonitrile-0.1 M ammonium acetate over 15 min, 0.5 mL/min) Rt 6.57 min (97%).

後処理

  1. customThe layers were partitioned
  2. extractionthe aqueous layer was extracted with ethyl acetate (1.2 L)
  3. washThe combined organic layers were washed with water (1.5 L)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe crude product was purified by flash chromatography on silica gel using 7:1 heptane

出典と根拠

ORDレコード
ord-7cc4c5a5b6944421acf0071ecf8ac517
出典データセット
uspto-grants-2005_07
特許番号
US06921763B2

反応ノート

読み込み中…