Glycerol → 1,7-Naphthyridin-8-amine

HRID 1772024ノート

反応式

HRID 1772024 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[C:2]=1[NH2:8].O[CH2:10][CH:11]([CH2:13]O)O.[N+](C1C=C(S([O-])(=O)=O)C=CC=1)([O-])=O.[Na+].S(=O)(=O)(O)O.[OH-].[Na+]>O>[N:7]1[C:3]2[C:4](=[CH:5][CH:6]=[N:1][C:2]=2[NH2:8])[CH:13]=[CH:11][CH:10]=1

参加物

7

反応物 5

HCID 753GlycerolHCID 1118Sulfuric AcidHCID 99562,3-DiaminopyridineHCID 14798Sodium HydroxideHCID 31389Sodium 3-nitrobenzenesulfonate

生成物 1

HCID 27370371,7-Naphthyridin-8-amine収率 39%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
135 °C

実験手順

A mixture of pyridine-2,3-diamine (5.0 g, 45.9 mmol), glycerol (21.1 g, 229 mmol), sodium 3-nitrobenzenesulphonate (20.6 g, 91.7 mmol), sulfuric acid (20 mL) and water (30 mL) was heated to 135° C. and stirred for 16 h. The mixture was cooled to room temperature and then poured into ice/water (150 g). The mixture was adjusted to pH ˜9 with saturated NaOH aqueous solution. Then the mixture was extracted with EtOAc (3×100 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduce pressure to give the crude product, which was purified by silica gel column (eluting with PE/EtOAc v/v 2:1) to give 1,7-naphthyridin-8-amine as a yellow solid (2.6 g, yield 39%). ESI MS: m/z 146.1 [M+H]+.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThen the mixture was extracted with EtOAc (3×100 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas purified by silica gel column (
  7. washeluting with PE/EtOAc v/v 2:1)

出典と根拠

ORDレコード
ord-99e58f7230e347de97eac17f96437fd5
出典データセット
uspto-grants-2016_02
特許番号
US09249162B2

反応ノート

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