Triethylamine → HCID 11508173, compound

HRID 735241Notes

Reaction equation

HRID 735241 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10](Cl)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([CH3:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:6](=[O:13])[NH:7]2.C([O-])([O-])=O.[K+].[K+].[CH2:28]([N:30](CC)[CH2:31]C)C.Cl.CNC>CC#N>[Cl:1][C:2]1[CH:11]=[C:10]([N:30]([CH3:31])[CH3:28])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([CH3:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:6](=[O:13])[NH:7]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 11638332HCID 11638332, compound

Product 1

HCID 11508173HCID 11508173, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5,7-dichloro-3-methyl-3-phenyl-1H-quinoline-2,4-dione (1.00 g, 3.12 mmol) in MeCN (10 mL) were added K2CO3 (0.65 g, 4.68 mmol), triethylamine (0.65 mL, 4.68 mmol), and dimethylamine hydrochloride (0.35 g, 7.80 mmol) at room temperature. The reaction mixture was then heated for 10 hours at reflux temperature. After the reaction completed, the solvent was removed. The residue was diluted with 1N HCl solution and extracted with ethyl acetate (100 mL×2). The organic phase was dried over magnesium sulfate and concentrated in vacuo. The crude was purified by a column chromatography on silica gel to give the objective compound (0.67 g, 65%): 1H NMR (200 MHz, CDCl3) δ 1.89 (s, 3H, CH3), 2.64 (s, 6H, 2NCH3), 6.29 (d, J=2.03 Hz, 1H, ArH), 6.49 (d, J=2.03 Hz, 1H, ArH), 7.23-7.33 (m, 5H, ArH), 9.13 (br s, 1H, NH); m.p. 224-226° C.; MS(EI) m/e 328 [M+], 313, 196, 132; HRMS m/e cacld. for C18H17N2O2Cl 328.0979, found 328.0979.

Workup

  1. temperatureThe reaction mixture was then heated for 10 hours
  2. temperatureat reflux temperature
  3. customthe solvent was removed
  4. additionThe residue was diluted with 1N HCl solution
  5. extractionextracted with ethyl acetate (100 mL×2)
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude was purified by a column chromatography on silica gel

Sources & evidence

ORD record
ord-b3ed995d4991413093fdde097db76e32
Source dataset
uspto-grants-2009_09
Patent number
US07592457B2

Reaction notes

Loading…