Acetic Anhydride → HCID 22648244, compound

HRID 1872621Notes

Reaction equation

HRID 1872621 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-6e4b2ca2d9fe4e0f882d7bcd0675a64f
Source dataset
uspto-grants-2000_08
Patent number
US06110929

Reaction notes

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