Ammonia → 2-Hydroxyquinolin-8-yl acetate

HRID 2112744Notes

Reaction equation

HRID 2112744 reaction equation
[N+]1([O-])C2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:11])[CH:4]=[CH:3]C=1.[NH3:13].[C:14]([O:17][C:18](=[O:20])[CH3:19])(=O)[CH3:15]>>[C:18]([O:17][C:14]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:15]=1[NH:13][C:9](=[O:11])[CH:8]=[CH:7]2)(=[O:20])[CH3:19]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 7918Acetic AnhydrideHCID 143128-Hydroxyquinoline N-oxide

Product 1

HCID 2682402-Hydroxyquinolin-8-yl acetate

Procedure

Quinolin-8-ol 1-oxide (20 g, 124 mmol) in acetic anhydride (200 ml) was stirred at 90° C. for 5 hours. Then the reaction mixture was poured into water/ice mixture (1.5 L), and made neutral by addition of conc. aq. NH3. The precipitate formed was collected by filtration and washed with water. The crude product was purified by suspending in propan-2-ol and addition of petroleum ether to give 2-oxo-1,2-dihydroquinolin-8-yl acetate. 2-Oxo-1,2-dihydroquinolin-8-yl acetate was heated in conc. aq. HCl (200 ml) at 90° C. for 4 hours. The reaction mixture was poured into ice-cold water (400 ml), and the precipitate formed was collected by filtration and washed with water. Recrystallization from propan-2-ol/petroleum ether afforded the subtitle compound (14.1 g, 70%).

Workup

  1. customThe precipitate formed
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. customThe crude product was purified
  5. additionaddition of petroleum ether

Sources & evidence

ORD record
ord-a502f6f7cc834615b8ccbcb2240a9129
Source dataset
uspto-grants-2009_04
Patent number
US07524856B2

Reaction notes

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