Glycerol → 1,7-Naphthyridin-8-amine

HRID 1772024

반응식

HRID 1772024 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-99e58f7230e347de97eac17f96437fd5
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249162B2

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