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

HRID 1042727ノート

反応式

HRID 1042727 の反応式
[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

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 22728543Water ethylacetateHCID 178524411HCID 178524411、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d67995f741e54ed285268ef3321a37bc
出典データセット
uspto-grants-2013_10
特許番号
US08557996B2

反応ノート

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