Sodium Hydroxide → 2-Ethyloxazolo[4,5-c]quinoline

HRID 48276

Reaction equation

HRID 48276 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[OH:13])=[CH:10][CH:9]=[CH:8][CH:7]=2.[C:14](OC(=O)CC)(=O)[CH2:15][CH3:16].[OH-].[Na+]>O>[CH2:15]([C:16]1[O:13][C:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:5]=[CH:4][C:3]=2[N:2]=1)[CH3:14]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31263Propionic anhydrideHCID 178479094HCID 178479094, compound

Product 1

HCID 226482852-Ethyloxazolo[4,5-c]quinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Aminoquinolin-4-ol hydrochloride (6 g) was refluxed with propanoic anhydride (8 eq.) until analysis by thin layer chromatography indicated that the reaction was complete. The reaction mixture was cooled, diluted with ice and water, made basic with 10% sodium hydroxide and then extracted with dichloromethane. The extract was washed with water and brine, dried over magnesium sulfate and then concentrated under vacuum. The residue was purified by column chromatography (silica gel eluting with methanol/ethyl acetate) to provide 4.0 g of 2-ethyloxazolo[4,5-c]quinoline.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with dichloromethane
  3. washThe extract was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by column chromatography (silica gel eluting with methanol/ethyl acetate)

Sources & evidence

ORD record
ord-451dc9c0563a428e9d2ff2a42e8d9942
Source dataset
uspto-grants-2004_03
Patent number
US06703402B2

Linked notes

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