Ethyl Acetate → Ethyl 6-chloro-5-hydroxynicotinate

HRID 509403

反応式

HRID 509403 の反応式
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].C1C(=O)N([Cl:20])C(=O)C1.CCOC(C)=O>CN(C=O)C.CCCCCC>[Cl:20][C:3]1[C:2]([OH:1])=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]=1

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 31398ChlorosuccinimideHCID 910016Ethyl 5-hydroxynicotinate

生成物 1

HCID 86687988Ethyl 6-chloro-5-hydroxynicotinate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8058Hexane溶媒

反応条件

温度
80 °C

実験手順

To a stirred mixture of ethyl 5-hydroxynicotinate (20 g, 0.119 mol, in DMF (200.0 mL) was added NCS (19.18 g, 0.143 mol, Aldrich). The reaction mixture was stirred for 2 h at 80° C. After completion of the reaction (monitored by TLC, 30% EtOAc in hexane), the reaction mixture was quenched with sat'd NaHCO3 solution (50 mL) and extracted with EtOAc (500 mL×3). The combined organic layers were dried over anhydrous sodium sulfate, and purified by column chromatography, silica gel (100-200 mesh), using 10-15% EtOAc in petroleum ether as the eluent to give the title compound as a solid. 1H NMR (400 MHz, CDCl3) δ: 8.61 (d, J=2.1 Hz, 1H), 7.92 (d, J=1.8 Hz, 1H), 5.94 (br. s., 1H), 4.53 (q, J=6.9 Hz, 2H), 1.43 (t, J=7.2 Hz, 3H). MS (ESI, positive ion) m/z: 202.1 (M+H).

後処理

  1. customthe reaction mixture was quenched with sat'd NaHCO3 solution (50 mL)
  2. extractionextracted with EtOAc (500 mL×3)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. custompurified by column chromatography, silica gel (100-200 mesh)

出典と根拠

ORDレコード
ord-885dc2a6128d4ce4ac30f33dc016968a
出典データセット
uspto-grants-2015_08
特許番号
US09096527B2

関連ノート

読み込み中…