Methanol → Methyl 2-(6-aminopyridin-3-yl)-2-methylpropanoate

HRID 1602993ノート

反応式

HRID 1602993 の反応式
Cl.[NH2:2][C:3]1[N:8]=[CH:7][C:6]([C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.OS(O)(=O)=O.[CH3:20]O>>[NH2:2][C:3]1[N:8]=[CH:7][C:6]([C:9]([CH3:14])([CH3:13])[C:10]([O:12][CH3:20])=[O:11])=[CH:5][CH:4]=1

参加物

4

反応物 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 671308492-(6-Aminopyridin-3-yl)-2-methylpropanoic acid hydrochloride

生成物 1

HCID 21998700Methyl 2-(6-aminopyridin-3-yl)-2-methylpropanoate

実験手順

A solution of 2-(6-aminopyridin-3-yl)-2-methylpropanoic acid hydrochloride (35.0 g, 0.162 mmol) and concentrated H2SO4 (5 mL) in MeOH (250 mL) was heated at reflux overnight. After cooling to ambient temperature, the reaction was quenched cautiously with saturated aqueous NaHCO3 and concentrated in vacuo. The residue was partitioned between ethyl acetate and water, the organic phase separated and the aqueous phase re-extracted with ethyl acetate (×3). The combined organic extract was washed with brine, dried (MgSO4) and concentrated in vacuo. The residue (31.6 g, 100%) was judged pure by a combination of TLC and 1H nmr analysis and was used without further purification in the subsequent reaction.

後処理

  1. temperatureat reflux overnight
  2. customthe reaction was quenched cautiously with saturated aqueous NaHCO3
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between ethyl acetate and water
  5. customthe organic phase separated
  6. extractionthe aqueous phase re-extracted with ethyl acetate (×3)
  7. extractionThe combined organic extract
  8. washwas washed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo
  11. customwas used without further purification in the subsequent reaction

出典と根拠

ORDレコード
ord-f3b7f4a8b5484f1fbc447597a5654597
出典データセット
uspto-grants-1999_11
特許番号
US05985892

反応ノート

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