Acetic Anhydride → HCID 22648244, compound

HRID 393932Notes

Reaction equation

HRID 393932 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[OH:12])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:13](OC(=O)C)(=O)[CH3:14].[OH-].[Na+]>O>[CH3:13][C:14]1[O:12][C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 178507989HCID 178507989, compound

Product 1

HCID 22648244HCID 22648244, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Aminoquinolin-4-ol (6 g) was refluxed with acetic 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 5.1 g of 2-methyloxazolo[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-5e15c382952d49d79d9c8e3880f89cae
Source dataset
uspto-grants-2004_10
Patent number
US06809203B2

Reaction notes

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