Sodium Iodide → HCID 10806148, compound

HRID 977180Notes

Reaction equation

HRID 977180 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:19])=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+].[I-].[Na+].Cl[CH2:28][C:29](=[O:31])[CH3:30]>CN(C)C=O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:19][CH2:28][C:29](=[O:31])[CH3:30])=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6571ChloroacetoneHCID 516892Sodium BicarbonateHCID 546974683-Phenyl-4-hydroxy-7-chloroquinolin-2(1H)-one

Product 1

HCID 10806148HCID 10806148, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 7-chloro-4-hydroxy-3-phenyl-2(1H)-quinolone (0.50 g 0.0018 mol), sodium hydrogen carbonate (1.55 g, 0.018 mol) and sodium iodide (0.20 g) in N,N-dimethylformamide (20 ml) was added chloroacetone (0.20 g, 0.0020 mol). The reaction was stirred for 24 h, then the product was precipitated by the addition of water (50 ml). The product was collected by filtration, washed with water (3×10 ml) and dried under vacuum at 60° C. Recrystallisation from ethyl acetate/60-80 petrol gave a white crystalline solid; yield=390 mg, mp=185°-186° C.; Found: C, 66.20; H, 4.33; N, 4.20; C18H14ClNO3 requires C, 65.96; H, 4.31; N, 4.27. δ (360 MHz, DMSO-d6), 1.84 (3H, s, CH3CO), 4.26 (2H, s, CH2), 7.26 (1H, dd, J=8.7 and 2.1 Hz, 6-H), 7.30-7.46 (6H, m, aromatics), 8.02 (1H, d, J=8.7 Hz, 5-H), 11.90(1H, s, br, NH). MS (CI) m/z=328 (MH)+.

Workup

  1. customthe product was precipitated by the addition of water (50 ml)
  2. filtrationThe product was collected by filtration
  3. washwashed with water (3×10 ml)
  4. customdried under vacuum at 60° C
  5. customRecrystallisation from ethyl acetate/60-80 petrol
  6. customgave a white crystalline solid

Sources & evidence

ORD record
ord-cb63506e867b440c99becc4422a8e255
Source dataset
uspto-grants-1997_03
Patent number
US05614532

Reaction notes

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