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

HRID 1728188노트

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HRID 1728188 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2d965dbf63c241e483c8dc30a2df0a20
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07495007B2

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