Methyl iodide → Methyl 5-chloro-1-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate

HRID 1042727노트

반응식

HRID 1042727 반응식
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([OH:11])=C([CH:10]=1)C(O)=O.[C:12](=O)([O-])[O-].[Cs+].[Cs+].CI.C[CH2:21][O:22][C:23]([CH3:25])=[O:24].O>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[C:25]([C:23]([O:22][CH3:21])=[O:24])[C:5](=[O:11])[N:4]([CH3:12])[CH:3]=1

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 22728543Water ethylacetateHCID 178524411HCID 178524411, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a suspension of 5-chloro-2-hydroxynicotinic acid (2.0 g, 12 mmol) and cesium carbonate (8.2 g, 26 mmol) in 50 mL DMF was added MeI (1.6 ml, 26 mmol). The reaction was allowed to stir for approximately 12 h. The cloudy yellow mixture was added to EtOAc/water. The organic layer was removed and the aqueous layer was extracted three times with EtOAc. The combined organic layers were washed once with water and brine, 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 an orange solid. MS (m/z): 202.0 (M+H)+. Calc'd for C8H8ClNO3: 201.61.

후처리

  1. customThe organic layer was removed
  2. extractionthe aqueous layer was extracted three times with EtOAc
  3. washThe combined organic layers were washed once with water and brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an orange-yellow solid
  8. customThe material was partitioned between 1N HCl and EtOAc
  9. washThe organic layer was washed twice with 1N HCl
  10. dry with materialdried with Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d67995f741e54ed285268ef3321a37bc
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557996B2

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