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

HRID 1168759Notes

Reaction equation

HRID 1168759 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-b0a3ee03a1f040bab759611f05b73f50
Source dataset
uspto-grants-2003_09
Patent number
US06627638B2

Reaction notes

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