2-Acetylbutyrolactone → HCID 12414937, compound

HRID 2222275Notes

Reaction equation

HRID 2222275 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9]([CH:12]1[CH2:17][CH2:16]O[C:13]1=[O:14])(=O)[CH3:10].[OH-].[Na+].P(Cl)(Cl)([Cl:22])=O>>[Cl:22][CH2:16][CH2:17][C:12]1[C:13](=[O:14])[N:3]2[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]2=[N:1][C:9]=1[CH3:10]

Participants

5

Reactant 4

HCID 106012-AcetylbutyrolactoneHCID 14798Sodium HydroxideHCID 153472-Amino-3-methylpyridineHCID 24813Phosphorus oxychloride

Product 1

HCID 12414937HCID 12414937, compound

Conditions

Temperature
100 °C

Procedure

To a solution of 2-amino-3-picoline (3.3 9, 30 mmol) in phosphorus oxychloride (11 ml) was added 2-acetylbutyrolactone (3.25 ml, 30 mmol). The mixture was heated at 100° C. for 18 hours, cooled, poured on ice, made basic with a 2N sodium hydroxide solution and extracted with ethyl acetate. The organic layer was separated, dried, concentrated and purified by silica gel column chromatography (dichloromethane/methanol=95/5). Yield 2.5 g (35%) of white solid.

Workup

  1. temperaturecooled
  2. additionpoured on ice
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (dichloromethane/methanol=95/5)

Sources & evidence

ORD record
ord-1b01db5cc0484f358f63ca44e581c836
Source dataset
uspto-grants-2008_05
Patent number
US07371769B2

Reaction notes

Loading…