Glycerol → 1,5-Naphthyridin-2-amine

HRID 868967ノート

反応式

HRID 868967 の反応式
[N:1]1[CH:6]=[C:5]([NH2:7])[CH:4]=[CH:3][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:1]1[C:6]2[C:5](=[N:7][CH:10]=[CH:11][CH:13]=2)[CH:4]=[CH:3][C:2]=1[NH2:8]

参加物

7

反応物 5

HCID 753GlycerolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 203142,5-PyridinediamineHCID 31389Sodium 3-nitrobenzenesulfonate

生成物 1

HCID 5893551,5-Naphthyridin-2-amine収率 40.6%

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-2,5-diamine (5.2 g, 71% pure, 33.9 mmol), glycerol (15.6 g, 169.5 mmol), sodium 3-nitrobenzenesulphonate (15.2 g, 67.8 mmol), sulfuric acid (20 mL), and water (30 mL) was heated to 135° C. and stirred at this temperature for 16 h. The mixture was cooled to room temperature and then poured into ice water (150 g). The pH of the reaction mixture was adjusted to 9 with saturated sodium hydroxide aqueous solution. Then the mixture was extracted with EtOAc (3×100 mL). The extracts were dried over sodium sulfate, concentrated under reduce pressure to give the crude product. The crude product was purified by column chromatography to give 2.0 g of 1,5-naphthyridin-2-amine as a yellow solid.

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 extracts were dried over sodium sulfate
  4. concentrationconcentrated
  5. customto give the crude product
  6. customThe crude product was purified by column chromatography

出典と根拠

ORDレコード
ord-3f57624f5d0f4e39b04916c3700b5cd7
出典データセット
uspto-grants-2015_03
特許番号
US08969349B2

反応ノート

読み込み中…