Glycerol → 1,6-Naphthyridine

HRID 249312ノート

反応式

HRID 249312 の反応式
O[CH2:2][CH:3]([CH2:5]O)O.[N+](C1C=CC=CC=1)([O-])=O.S(=O)(=O)(O)O.[NH2:21][C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1.[OH-].[Na+]>O>[N:21]1[C:22]2[C:23](=[CH:24][N:25]=[CH:26][CH:27]=2)[CH:5]=[CH:3][CH:2]=1

参加物

7

反応物 5

HCID 753GlycerolHCID 1118Sulfuric AcidHCID 17274-AminopyridineHCID 7416NitrobenzeneHCID 14798Sodium Hydroxide

生成物 1

HCID 674881,6-Naphthyridine収率 18%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Glycerol (138.15 g, 1.5 mol) was added dropwise to an ice-cold mixture of "sulfo-mix" (a mixture of nitrobenzene and fuming sulfuric acid, see: Utermohlen, W. P., J. Org. Chem, 1943 8, 544). Addition of 4-aminopyridine (56.46 g, 0.6 mol) was followed by a rapid dropwise addition of water (225 ml), which caused a rise in temperature to 80°; the reaction mixture was allowed to stir until it became homogeneous, and was subsequently heated to 135° for 48 hours. It was then allowed to cool, poured into 1 l ice water, and the pH was adjusted to 13 by the addition of sodium hydroxide pellets. The resulting thick precipitate was removed by filtration, and the filtrate was extracted with methylene chloride (2×2 l). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated to yield a crude product, which was purified by column chromatography (98:2 methylene chloride:methanol). The title product was obtained as an amber oil which crystallized upon standing (13.7 g, 0.11 mol, 18% yield).

後処理

  1. additionmix" (
  2. customto 80°
  3. temperaturewas subsequently heated to 135° for 48 hours
  4. temperatureto cool
  5. customThe resulting thick precipitate was removed by filtration
  6. extractionthe filtrate was extracted with methylene chloride (2×2 l)
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto yield a crude product, which
  11. customwas purified by column chromatography (98:2 methylene chloride:methanol)

出典と根拠

ORDレコード
ord-47fec2031798471085704012fec77a39
出典データセット
uspto-grants-1993_05
特許番号
US05214051

反応ノート

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