Glycerol → 2-Methyl-1,5-naphthyridine

HRID 876833Notes

Reaction equation

HRID 876833 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[CH2:9](O)[CH:10](O)[CH2:11]O.OS(O)(=O)=O.[OH-].[Na+]>O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[CH:9][CH:10]=[CH:11][N:8]=2)[N:7]=1

Participants

6

Reactant 4

HCID 753GlycerolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 2433135-Amino-2-methylpyridine

Product 1

HCID 5890332-Methyl-1,5-naphthyridineYield 45.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 6-methylpyridin-3-amine (8-1) (4.8 g, 44.4 mmol) and propane-1,2,3-triol (20 g, 222 mmol) in 5 mL of H2O was stirred at room temperature for 5 min, then concentrated H2SO4 (47 g, 488 mmol) was added dropwise within 20 min at room temperature. After addition, the reaction mixture was stirred at 150° C. for 30 min. After cooled to room temperature, the mixture was poured into water, adjusted with 6 N NaOH to pH 13, then extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, concentrated and purified by chromatography on silica gel to afford the title compound (2.9 g). MS: 145 (M+1)+.

Workup

  1. additionAfter addition
  2. stirringthe reaction mixture was stirred at 150° C. for 30 min
  3. temperatureAfter cooled to room temperature
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-3249888953b340e199e87a9b3dc7d61a
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

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