2,6-Diamino-3-nitropyridine → 3-Phenylpyrido[2,3-b]pyrazin-6-ylamine

HRID 215796

反応式

HRID 215796 の反応式
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([NH2:11])[N:3]=1.O.[C:13]1([C:19]([CH:21]=O)=O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C.[Ni]>[C:13]1([C:19]2[N:1]=[C:2]3[N:3]=[C:4]([NH2:11])[CH:5]=[CH:6][C:7]3=[N:8][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

5

反応物 2

HCID 3199982,6-Diamino-3-nitropyridineHCID 12215922Glyoxal, phenyl-, hydrate

生成物 1

HCID 121331983-Phenylpyrido[2,3-b]pyrazin-6-ylamine

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 702Ethanol溶媒2 回

実験手順

A solution of 1.22 g of 2,6-diamino-3-nitropyridine (7.92 mmol) in 210 ml of ethanol is hydrogenated with Raney nickel as catalyst at 50° C. and 5 bar. After the hydrogenation is complete, the catalyst is filtered off with suction through a glass fibre filter. Before the filtration, 1.68 g of phenylglyoxal hydrate (11.03 mmol) are introduced into 50 ml of ethanol in the receiver. The catalyst is then filtered off under nitrogen as protective gas, and the hydrogenation solution is sucked directly into the reaction flask. The greenish blue reaction mixture is heated under reflux under nitrogen for 30 min. The mixture is allowed to cool, and the solvent is removed in vacuo. A dark brown solid is finally obtained. Purification by column chromatography on silica gel (mobile phase dichloromethane/methanol mixture) affords a pale yellow crystalline solid.

後処理

  1. filtrationthe catalyst is filtered off with suction through a glass fibre filter
  2. filtrationThe catalyst is then filtered off under nitrogen as protective gas
  3. customThe greenish blue reaction mixture
  4. temperatureis heated
  5. temperatureunder reflux under nitrogen for 30 min
  6. temperatureto cool
  7. customthe solvent is removed in vacuo
  8. customA dark brown solid is finally obtained
  9. customPurification by column chromatography on silica gel (mobile phase dichloromethane/methanol mixture)
  10. customaffords a pale yellow crystalline solid

出典と根拠

ORDレコード
ord-c099f283504f477e828fc227eb9fd20b
出典データセット
uspto-grants-2012_06
特許番号
US08193186B2

関連ノート

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