Acetic Acid → 2-Methyl-4-methoxypyridine-N-oxide

HRID 346051

反応式

HRID 346051 の反応式
[Na].[N+]([C:5]1[CH:10]=[CH:9][N+:8]([O-:11])=[C:7]([CH3:12])[CH:6]=1)([O-])=O.[C:13](O)(=[O:15])C.C([O-])(O)=O.[Na+]>CO.O>[CH3:13][O:15][C:5]1[CH:10]=[CH:9][N+:8]([O-:11])=[C:7]([CH3:12])[CH:6]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 95291Pyridine, 2-methyl-4-nitro-, 1-oxideHCID 516892Sodium BicarbonateHCID 5360545Sodium

生成物 1

HCID 107018932-Methyl-4-methoxypyridine-N-oxide

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

With stirring, sodium pellets (3.95 g, 0.172 mol), maintained dry under hexane, were added to 540 ml dry methanol, under N2. Following dissolution, the mixture was diluted with 900 ml methanol, 4-nitro-2-methylpyridine N-oxide (26.0 g, 0.169 mol) was added, and the mixture heated at reflux for 1 hour, cooled to room temperature and acidified with 18 ml glacial acetic acid. After stirring 15 minutes, the reaction mixture was stripped of solvent, the orange residue taken up in 300 ml of H2O, neutralized with saturated NaHCO3, reconcentrated to dryness, and the residue triturated 5×50 ml of ethanol. The ethanol triturates were combined, stripped to dryness, and the residue restripped 3×50 ml toluene to yield solids (36.1 g) which were chromatographed on silica gel using 6:1 CH2Cl2 :CH3OH as eluant to yield purified title product, 21.14 g; MS 139 (M+).

後処理

  1. customdry under hexane
  2. additionwere added to 540 ml dry methanol, under N2
  3. dissolutiondissolution
  4. additionwas added
  5. temperaturethe mixture heated
  6. temperatureat reflux for 1 hour
  7. stirringAfter stirring 15 minutes
  8. customthe residue triturated 5×50 ml of ethanol

出典と根拠

ORDレコード
ord-03c21b2224684d0684ff0a449d751577
出典データセット
uspto-grants-1991_10
特許番号
US05059609

関連ノート

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