Glycerol → 1,7-Naphthyridin-8-amine

HRID 1615658

반응식

HRID 1615658 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

HCID 27370371,7-Naphthyridin-8-amine수율 39%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
135 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-e4d98668244840ff91d551adbbe190b8
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765760B2

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