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

HRID 1024711

반응식

HRID 1024711 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

반응 조건

온도
60 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e3f8d293e72b40c4b8e6f5c53e32f9d2
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722930B2

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