Glycerol → 1,5-Naphthyridin-2-amine

HRID 868967노트

반응식

HRID 868967 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

HCID 5893551,5-Naphthyridin-2-amine수율 40.6%

시약·촉매·용매 1

HCID 962Water용매

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온도
135 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3f57624f5d0f4e39b04916c3700b5cd7
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969349B2

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