Ethylene Glycol → 5-(4-Chlorophenyl)-6-(2-hydroxyethoxy)nicotinic acid

HRID 1025998ノート

反応式

HRID 1025998 の反応式
[CH2:1]([OH:4])[CH2:2][OH:3].[H-].[Na+].Cl[C:8]1[N:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][C:9]=1[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1.O>CN(C=O)C>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]([C:9]2[C:8]([O:3][CH2:2][CH2:1][OH:4])=[N:13][CH:12]=[C:11]([CH:10]=2)[C:14]([OH:16])=[O:15])=[CH:22][CH:21]=1

参加物

6

反応物 4

HCID 174Ethylene GlycolHCID 962WaterHCID 24758Sodium hydride2 回HCID 866191836-Chloro-5-(4-chlorophenyl)-3-pyridinecarboxylic acid

生成物 1

HCID 666786215-(4-Chlorophenyl)-6-(2-hydroxyethoxy)nicotinic acid収率 41.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of ethane-1,2-diol (301 mg, 270 μA, 4.84 mmol) in dried DMF (6 mL) was added sodium hydride (232 mg, 4.84 mmol) and the reaction mixture was stirred at room temperature for 15 minutes. The resulting solution was added slowly to a solution of 6-chloro-5-(4-chlorophenyl)-3-pyridinecarboxylic acid (CAN 1012792-56-1; 0.590 g, 2.2 mmol) in dried DMF (6 mL) and stirred at 80° C. for 4 h. More sodium hydride (106 mg, 2.2 mmol) was added and at room temperature and stirring at 80° C. commenced for another 2 h. Water was added and DMF was evaporated. The residue was dissolved in water; acidified with 3M HCl to pH 3. The suspension was filtered; the filter cake was washed with water and dried under high vacuo. The crude material was purified by flash chromatography (ReproFlash Acidosil-S, 50 g, 50% to 100% ethylacetate in heptane) to give 0.27 g (41%) of the title compound as a white solid; MS (ESI): 292.1 (M−H)−.

後処理

  1. stirringstirred at 80° C. for 4 h
  2. stirringstirring at 80° C.
  3. waitcommenced for another 2 h
  4. customDMF was evaporated
  5. dissolutionThe residue was dissolved in water
  6. filtrationThe suspension was filtered
  7. washthe filter cake was washed with water
  8. customdried under high vacuo
  9. customThe crude material was purified by flash chromatography (ReproFlash Acidosil-S, 50 g, 50% to 100% ethylacetate in heptane)

出典と根拠

ORDレコード
ord-a7486a0e519c4cc881132eddc6037c5d
出典データセット
uspto-grants-2014_05
特許番号
US08729105B2

反応ノート

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