Glycerol → 1,5-Naphthyridin-2-amine
Reaction equation
[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]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 135 °C
Procedure
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.
Workup
- temperatureThe mixture was cooled to room temperature
- extractionThen the mixture was extracted with EtOAc (3×100 mL)
- dry with materialThe extracts were dried over sodium sulfate
- concentrationconcentrated
- customto give the crude product
- customThe crude product was purified by column chromatography
Sources & evidence
- ORD record
- ord-3f57624f5d0f4e39b04916c3700b5cd7
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969349B2
Reaction notes
Loading…