Acetic Acid → HCID 69065924, compound

HRID 1821111Notes

Reaction equation

HRID 1821111 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12](C(=O)C)=[C:13]3[C:18]=2[NH:17][C:16](=[O:19])[CH:15]=[CH:14]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23]([OH:26])(=O)[CH3:24].I([Cl:30])(=O)=O.I(Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1>O>[Cl:30][CH2:24][C:23]([N:17]1[C:18]2[C:13](=[CH:12][CH:11]=[CH:10][C:9]=2[O:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:14]=[CH:15][C:16]1=[O:19])=[O:26]

Participants

5

Reactant 3

HCID 176Acetic Acid2×HCID 133754445-Acetyl-8-(benzyloxy)-1,2-dihydroquinolin-2-oneHCID 56924451Trimethylbenzylammonium Dichloroiodate

Product 1

HCID 69065924HCID 69065924, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
67.5 °C

Procedure

A 3 L, 4-necked flask equipped with a mechanical stirrer, thermometer, addition funnel and refluxing condenser is charged with 40 g 8-(phenylmethoxy)-5-acetyl-(1H)-quinolin-2-one and 800 mL acetic acid under an atmosphere of nitrogen. To this yellow solution is added 94.93 g benzyl-trimethylammoniumdichloroiodate and 400 mL acetic acid. The resulting suspension is heated under stirring to an internal temperature of 65-70° C. The mixture is stirred at this internal temperature until an in-process control shows complete conversion to 5-chloroacetyll-8-phenylmethoxy-(1H)-quinolin-2-one. Then the mixture is cooled to an internal temperature of 40-45° C. Within 30-60 minutes, 600 mL water is added. The resulting suspension is stirred at room temperature for 30-60 minutes and then filtered. The solid residue is washed with 200 mL water in several portions and then added to 2000 L ethyl acetate in a 3 L, 4-necked flask equipped with a mechanical stirrer, thermometer and refluxing condenser. This mixture is heated to reflux and refluxed for 15 minutes. The mixture is cooled to an internal temperature of 0-2° C. and stirred at this internal temperature for 2 hours. The mixture is filtered and washed with 250 mL water in several portions, and dried overnight in a vacuum drier at 60° C. to give the title compound with a yield of 39.64 g.

Workup

  1. customA 3 L, 4-necked flask equipped with a mechanical stirrer
  2. additionthermometer, addition funnel
  3. temperaturerefluxing condenser
  4. temperatureThe resulting suspension is heated
  5. stirringThe mixture is stirred at this internal temperature until an in-process control
  6. temperatureThen the mixture is cooled to an internal temperature of 40-45° C
  7. stirringThe resulting suspension is stirred at room temperature for 30-60 minutes
  8. filtrationfiltered
  9. washThe solid residue is washed with 200 mL water in several portions
  10. additionadded to 2000 L ethyl acetate in a 3 L, 4-necked flask
  11. customequipped with a mechanical stirrer
  12. temperaturethermometer and refluxing condenser
  13. temperatureThis mixture is heated
  14. temperatureto reflux
  15. temperaturerefluxed for 15 minutes
  16. temperatureThe mixture is cooled to an internal temperature of 0-2° C.
  17. stirringstirred at this internal temperature for 2 hours
  18. filtrationThe mixture is filtered
  19. washwashed with 250 mL water in several portions
  20. customdried overnight in a vacuum drier at 60° C.

Sources & evidence

ORD record
ord-4a522b0d2c1c4079b5d28430a7bc17b8
Source dataset
uspto-grants-2009_10
Patent number
US07605267B2

Reaction notes

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