Benzene → Methyl 2-oxo-1,2-dihydropyridine-3-carboxylate

HRID 1199804ノート

反応式

HRID 1199804 の反応式
[O:1]=[C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=[CH:4][NH:3]1.S(=O)(=O)(O)O.[CH:16]1C=CC=CC=1>CO>[O:1]=[C:2]1[C:7]([C:8]([O:10][CH3:16])=[O:9])=[CH:6][CH:5]=[CH:4][NH:3]1

参加物

5

反応物 3

HCID 241BenzeneHCID 1118Sulfuric AcidHCID 691142-Hydroxynicotinic acid

生成物 1

HCID 579028Methyl 2-oxo-1,2-dihydropyridine-3-carboxylate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture containing 27.8 g of 1,2-dihydro-2-oxo-3-pyridinecarboxylic acid, 3.0 ml of concentrated sulfuric acid in 500 ml of methanol, and 300 ml of benzene are heated under reflux for 2.5 hours. A Dean-Stark trap is then attached, and the azeotrope collected is removed periodically in 25 ml fractions over a period of 28 hours. The remaining solvent is removed by evaporation under reduced pressure and the solid residue suspended in 500 ml of cold water. The suspension is filtered (from which unreacted starting material can be recovered) and the filtrate continuously extracted with methylene chloride. The extracts are concentrated under reduced pressure to yield the title compound as a white solid which, upon recrystallization from 1.4 L of benzene, yields 19.48 g (64%) of methyl 2-oxo-1,2-dihydro-3-pyridinecarboxylate: m.p. 148°-151° C.; NMR (DMSO-d6, 80 MHz) delta 3.72 (s, 3H), 6.25 (dd, 1H, J=7.1 Hz, J=6.3 Hz), 7.64 (dd, 1H, J=6.3 Hz, J=2.2 Hz), 8.03 (dd, 1H, J=7.1 Hz, J=2.2 Hz).

後処理

  1. temperatureare heated
  2. temperatureunder reflux for 2.5 hours
  3. customthe azeotrope collected
  4. customis removed periodically in 25 ml fractions over a period of 28 hours
  5. customThe remaining solvent is removed by evaporation under reduced pressure
  6. filtrationThe suspension is filtered
  7. custom(from which unreacted starting material can be recovered)
  8. extractionthe filtrate continuously extracted with methylene chloride
  9. concentrationThe extracts are concentrated under reduced pressure

出典と根拠

ORDレコード
ord-3b17fcc9b14f4e2a93158df4493e57f2
出典データセット
uspto-grants-1990_02
特許番号
US04902796

反応ノート

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