Acetyl chloride → HCID 10686612, compound

HRID 977169Notes

Reaction equation

HRID 977169 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[NH:5][C:4](=[O:13])[C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[H-].[Na+].[C:22](Cl)(=[O:24])[CH3:23]>O1CCCC1>[C:22]([NH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[NH:5][C:4](=[O:13])[C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 10707207HCID 10707207, compound

Product 1

HCID 10686612HCID 10686612, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-amino-7-chloro-3-phenyl-2(1H)-quinolone (Example 2) (0.3 g) in tetrahydrofuran (30 ml) was treated with sodium hydride (0.2 g, 80% disp. in oil). After 1 h, acetyl chloride (0.7 ml) was added and the reaction mixture was stirred for 2 h at room temperature then heated under reflux for 14 h. The reaction was partitioned between water and ethyl acetate. The organic phase was dried (MgSO4) and the solvent was removed in vacuo. The residue was suspended in 1N NaOH, and placed in an ultrasound bath for 5 mins. The aqueous phase was extracted with diethyl ether, acidified to pill and the precipitate produced was collected by filtration to give the title compound (0.080 g); mp 275°-277° C. (DMF-water). Found: C, 58.39; H, 4.83; N, 8.02. C17H13ClN2O2.2H2O requires C, 58.54; H, 4.91; N, 8.03%; δ (360 MHz, DMSO-d6) 1.88 (3H, s, CH3CO), 7.22-7.58 (8H, m, aromatics), 9.69 (1H, br s, NH), 12.06 (1H, br s, NH); m/z (EI) 312 (M+).

Workup

  1. temperaturethen heated
  2. temperatureunder reflux for 14 h
  3. customThe reaction was partitioned between water and ethyl acetate
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customthe solvent was removed in vacuo
  6. waitplaced in an ultrasound bath for 5 mins
  7. extractionThe aqueous phase was extracted with diethyl ether
  8. customthe precipitate produced
  9. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-1092b44d788b43e0918548d11d88fd41
Source dataset
uspto-grants-1997_03
Patent number
US05614532

Reaction notes

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