Methanol → Methyl 2-aminopyridine-3-carboxylate

HRID 18253

反応式

HRID 18253 の反応式
OS(O)(=O)=O.[NH2:6][C:7]1[N:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[CH3:16]O>>[NH2:6][C:7]1[N:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([O:11][CH3:16])=[O:10]

参加物

4

反応物 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 729302-Aminonicotinic acid

生成物 1

HCID 351633Methyl 2-aminopyridine-3-carboxylate収率 71%

実験手順

Concentrated H2SO4 (20 mL, 360 mmole) was added dropwise over 5 minutes to a suspension of 2-aminonicotinic acid (25 g, 181 mmole) in MeOH (400 mL), and the mixture was heated at reflux; a homogeneous solution formed within 5 min. After 72 h, the reaction was cooled to room temperature and concentrated under vacuum. The residue was basified with 1.0 N Na2CO3 (500 mL) (Gas evolution!) and extracted with EtOAc (500 mL). The organic layer was washed with brine, dried (Na2SO4), and concentrated to dryness to give the title compound (19.6 g, 71%) as a white solid: 1H NMR (400 MHz, CDCl3) δ 8.22 (dd, 1 H), 8.13 (dd, 1 H), 6.63 (dd, 1 H), 6.30 (br s, 2 H), 3.89 (s, 3 H).

後処理

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. customa homogeneous solution formed within 5 min
  4. concentrationconcentrated under vacuum
  5. extractionextracted with EtOAc (500 mL)
  6. washThe organic layer was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-66d6fe96f07b4ff6ac68c7b83d791ccd
出典データセット
uspto-grants-2010_06
特許番号
US07741339B2

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