Acetic Anhydride → HCID 22344493, compound

HRID 583834Notes

Reaction equation

HRID 583834 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[C:12](OC(=O)C)(=[O:14])[CH3:13]>N1C=CC=CC=1>[C:12]([O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2)(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 135441757Quinolin-5-ol

Product 1

HCID 22344493HCID 22344493, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-hydroxyquinoline (5.1 g) in pyridine (100 ml) was added acetic anhydride (4.0 ml) and then the reaction mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated. The residue was diluted with water. The diluted solution was extracted with ethyl acetate. The extracted solution was washed with water and a saturated aqueous solution of sodium chloride subsequently, dried over anhydrous magnesium sulfate and then concentrated. The residue was azeotropled with toluene to give the title compound (7.7 g) having the following physical data. The obtained compound was used without purification in the subsequent reaction.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionThe residue was diluted with water
  3. extractionThe diluted solution was extracted with ethyl acetate
  4. washThe extracted solution was washed with water
  5. dry with materiala saturated aqueous solution of sodium chloride subsequently, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fd39b9babe304f26953f0a2f586cac65
Source dataset
uspto-grants-2005_08
Patent number
US06924295B2

Reaction notes

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