Sodium Hydroxide → 5-Chloro-1-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid

HRID 1042728노트

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HRID 1042728 반응식
C[O:2][C:3]([C:5]1[C:6](=[O:13])[N:7]([CH3:12])[CH:8]=[C:9]([Cl:11])[CH:10]=1)=[O:4].[OH-].[Na+]>CO>[Cl:11][C:9]1[CH:10]=[C:5]([C:3]([OH:4])=[O:2])[C:6](=[O:13])[N:7]([CH3:12])[CH:8]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 68463468Methyl 5-chloro-1-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate

생성물 1

HCID 134428555-Chloro-1-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
80 °C

실험 절차

A mixture of methyl-5-chloro-1-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate (0.36 g, 1.8 mmol) and 2.0 mL each MeOH and 1N NaOH was heated in a sealed vial to 80° C. for 1 h. The reaction was cooled to ambient temperature, and the methanol was removed by a stream of nitrogen. Water (2 ml) was added and the solution was adjusted to pH 1 with 6N HCl. A thick white precipitate formed which was partitioned between water and dichloromethane. The organic layer was removed and the aqueous layer was extracted twice with dichloromethane. The combined organic layers were dried with Na2SO4, filtered, and concentrated to give an orange-yellow solid. The material was partitioned between 1N HCl and EtOAc. The organic layer was washed twice with 1N HCl, dried with Na2SO4, filtered, and concentrated to give the desired product as a light orange solid. MS (m/z): 188.0 (M+H)+. Calc'd for C7H6ClNO3: 187.58.

후처리

  1. temperatureThe reaction was cooled to ambient temperature
  2. customthe methanol was removed by a stream of nitrogen
  3. additionWater (2 ml) was added
  4. customA thick white precipitate formed which
  5. customwas partitioned between water and dichloromethane
  6. customThe organic layer was removed
  7. extractionthe aqueous layer was extracted twice with dichloromethane
  8. dry with materialThe combined organic layers were dried with Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give an orange-yellow solid
  12. customThe material was partitioned between 1N HCl and EtOAc
  13. washThe organic layer was washed twice with 1N HCl
  14. dry with materialdried with Na2SO4
  15. filtrationfiltered
  16. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5751e996e35d4659a4f6744d96506e01
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557996B2

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