Dimethylformamide → 3-chloro-5-formyl-2H-pyridine-1-carboxylic acid phenyl ester

HRID 1728188ノート

反応式

HRID 1728188 の反応式
P(Cl)(Cl)(Cl)=O.CN([CH:9]=[O:10])C.[C:11]1([O:17][C:18]([N:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH2:21]2)=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CC([O-])=O.[K+]>ClCCl.O>[C:11]1([O:17][C:18]([N:20]2[CH:25]=[C:24]([CH:9]=[O:10])[CH:23]=[C:22]([Cl:26])[CH2:21]2)=[O:19])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 517044Potassium AcetateHCID 575659013-chloro-2H-pyridine-1-carboxylic acid phenyl ester

生成物 1

HCID 575659313-chloro-5-formyl-2H-pyridine-1-carboxylic acid phenyl ester収率 96.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

Phosphorus oxychloride (5.4 g, 57.9 mmol) was added slowly to a stirred solution of DMF (8.9 mL, 116 mmol) in dichloromethane (10 mL) at 0° C. After addition, the solution was stirred at same temperature for 25 min., then transferred a solution of 3-chloro-2H-pyridine-1-carboxylic acid phenyl ester (5.67 g, 26.3 mmol) in anhydrous dichloromethane (50 mL) at 0° C. The ice bath was removed and stirring was continued at r.t. for 2 h, then the mixture was refluxed for 40 min. After the mixture was cooled to 0° C., an aqueous solution of KOAc (15 g, 153 mmol) in water (50 mL) was added slowly. The mixture was refluxed for 20 min., organic layer was separated, and aqueous layer was extracted with dichloromethane (50 mL). The organic layers were combined, washed with saturated NaHCO3, water and brine then dried over MgSO4, concentrated to give the crude product (Yield: 6.7 g).

後処理

  1. additionAfter addition
  2. customat 0° C
  3. customThe ice bath was removed
  4. stirringstirring
  5. waitwas continued at r.t. for 2 h
  6. temperaturethe mixture was refluxed for 40 min
  7. temperatureThe mixture was refluxed for 20 min.
  8. customorganic layer was separated
  9. extractionaqueous layer was extracted with dichloromethane (50 mL)
  10. washwashed with saturated NaHCO3, water and brine
  11. dry with materialthen dried over MgSO4
  12. concentrationconcentrated

出典と根拠

ORDレコード
ord-2d965dbf63c241e483c8dc30a2df0a20
出典データセット
uspto-grants-2009_02
特許番号
US07495007B2

反応ノート

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