Water → HCID 10041088, compound

HRID 977183Notes

Reaction equation

HRID 977183 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+].Br[CH2:26][C:27]#[N:28].O>CN(C)C=O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:19][CH2:26][C:27]#[N:28])=[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 962WaterHCID 11534BromoacetonitrileHCID 516892Sodium BicarbonateHCID 546974683-Phenyl-4-hydroxy-7-chloroquinolin-2(1H)-one

Product 1

HCID 10041088HCID 10041088, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-chloro-4-hydroxy-3-phenyl-2(1H)-quinolone (0.50 g, 1.84 mmol) in dimethyl formamide (50 ml) under nitrogen at room temperature, was added sodium hydrogen carbonate (1.50 g) followed by bromoacetonitrile (1.9 ml). The reaction mixture was stirred at room temperature for 16 h, then poured into water and extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with water (2×50 ml), dried (MgSO4), filtered and the solvent was removed in vacuo to leave an oily residue. Trituration with diethyl ether, followed by recrystallisation from an ethyl acetate, petrol (60-80) mixture, gave the title compound as a white solid (0.15 g). Mp 209°-211° C. Found: C, 65.60; H, 3.74; N, 8.75; C17H11N2O2Cl requires C, 65.71; H, 3.57; N, 9.02%. δ (360 MHz, DMSO-d6) 4.59 (2H, s, OCH2CN), 7.31 (1H, dd, J=8.63 Hz, J=2.10 Hz, 6-H), 7.40-7.49 (6H, m, Ph+8-H), 7.83 (1H, d, J=88.63 Hz, 5-H), 12.10 (1H, bs, NH). m/z (CI+), 311, (M+1).

Workup

  1. extractionextracted with ethyl acetate (3×50 ml)
  2. washThe combined organic layers were washed with water (2×50 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customto leave an oily residue
  7. customTrituration with diethyl ether, followed by recrystallisation from an ethyl acetate, petrol (60-80) mixture

Sources & evidence

ORD record
ord-834a605d01184e848955f65f9eced9aa
Source dataset
uspto-grants-1997_03
Patent number
US05614532

Reaction notes

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