Potassium Carbonate → 3,5-Bis-(5-cyano-pyridin-2-yloxy)-benzoic Acid Ethyl Ester

HRID 1024711ノート

反応式

HRID 1024711 の反応式
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10](=[O:19])[C:11]1[CH:16]=[C:15]([OH:17])[CH:14]=[C:13]([OH:18])[CH:12]=1)[CH3:8].Cl[C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][N:22]=1>CN(C=O)C>[CH2:7]([O:9][C:10](=[O:19])[C:11]1[CH:16]=[C:15]([O:17][C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][N:22]=2)[CH:14]=[C:13]([O:18][C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][N:22]=2)[CH:12]=1)[CH3:8]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 20098Benzoic acid, 3,5-dihydroxy-, ethyl esterHCID 51520946-Chloro-3-pyridinecarbonitrile

生成物 1

HCID 668186193,5-Bis-(5-cyano-pyridin-2-yloxy)-benzoic Acid Ethyl Ester収率 85.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

反応条件

温度
60 °C

実験手順

Potassium carbonate 2.1 g (15.2 mmol) dissolved in DMF solution was added to 3,5-dihydroxy-benzoic acid ethyl ester 1.5 g (8.2 mmol) dissolved in 15 ml of DMF. This was followed by dropwise addition of 6-chloro-nicotinonitrile 2.1 g (15.2 mmol) dissolved in 5 ml of DMF. After complete addition, the reaction mixture was stirred at 60° C. for 8-10 h. The reaction mixture was quenched with ice cold water and extracted with ethyl acetate. The organic layer was washed with water followed by brine, dried over anhydrous sodium sulphate and concentrated to afford a crude solid which was purified by column chromatography using hexane-ethyl acetate (10:2) to afford 2.5 g of the required product. 1H NMR (DMSO-d6): δ 1.30 (3H, t), 4.32 (2H, q), 7.35 (2H, d), 7.52 (1H, t), 7.68 (2H, d), 8.39 (2H, d), 8.69 (2H, s).

後処理

  1. additionAfter complete addition
  2. customThe reaction mixture was quenched with ice cold water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated
  7. customto afford a crude solid which
  8. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-e3f8d293e72b40c4b8e6f5c53e32f9d2
出典データセット
uspto-grants-2014_05
特許番号
US08722930B2

反応ノート

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