Acetic Anhydride → 5-Acetyl-8-(benzyloxy)-1,2-dihydroquinolin-2-one

HRID 883628Notes

Reaction equation

HRID 883628 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N+:9]2[O-])(=[O:3])[CH3:2].C(OC(=O)C)(=[O:25])C>>[C:1]([C:4]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:25])[NH:9]2)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 137448921-[8-(Benzyloxy)-1-oxo-1lambda~5~-quinolin-5-yl]ethan-1-one

Product 1

HCID 133754445-Acetyl-8-(benzyloxy)-1,2-dihydroquinolin-2-one

Conditions

Temperature
40 °C

Procedure

5-Acetyl-8-benzyloxyquinoline-N-oxide (10 gms/0.034 moles) was charged in acetic anhydride (20 ml) at 25-30° C. The resulting slurry was heated to 40° C. and stirred for 2 hours at 40° C. After completion of reaction, the reaction mass was cooled to 25-30° C., chilled to 0-5° C. and stirred for 30 minutes at 0-5° C. The resulting 5-Acetyl-8-benzyloxycarbostyril was isolated by filtration and washed with diisopropyl ether (50 ml), dried under vacuum at 60-65° C. for 2-3 hours. Yield-7 gms.

Workup

  1. customAfter completion of reaction
  2. temperaturethe reaction mass was cooled to 25-30° C.
  3. temperaturechilled to 0-5° C.
  4. stirringstirred for 30 minutes at 0-5° C

Sources & evidence

ORD record
ord-b13074c23ed34377bd200dea52e81b19
Source dataset
uspto-grants-2012_08
Patent number
US08236959B2

Reaction notes

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