Methanol → Methyl 6-amino-5-nitropyridine-3-carboxylate

HRID 854094ノート

反応式

HRID 854094 の反応式
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[CH3:14]O>OS(O)(=O)=O>[CH3:14][O:7][C:6](=[O:8])[C:5]1[CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]([NH2:1])=[N:3][CH:4]=1

参加物

4

反応物 2

HCID 887MethanolHCID 2718816-Amino-5-nitronicotinic acid

生成物 1

HCID 13768248Methyl 6-amino-5-nitropyridine-3-carboxylate収率 30%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

実験手順

A solution of 6-Amino-5-nitro-nicotinic acid (2) (15.2 g, 82.5 mmol) in MeOH (250 ml) and H2SO4 (conc. 25 ml) was heated at reflux for 5 h. The solution was concentrated in vacuo and the residue treated with saturated aqueous NaHCO3 solution until slightly basic. The resulting solid was collected by filtration, rinsed with H2O and dried in vacuo to give the product as a yellow solid (4.8 g, 25 mmol, 30%) that was used as is without further purification. TLC of the solid in DCM/MeOH (19:1) showed a less polar compound at Rf=0.5 compared to the baseline starting material.

後処理

  1. temperatureat reflux for 5 h
  2. concentrationThe solution was concentrated in vacuo
  3. additionthe residue treated with saturated aqueous NaHCO3 solution until slightly basic
  4. filtrationThe resulting solid was collected by filtration
  5. washrinsed with H2O
  6. customdried in vacuo

出典と根拠

ORDレコード
ord-3a9bc11470c14757bbd70905a068d729
出典データセット
uspto-grants-2007_08
特許番号
US07256287B2

反応ノート

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