Triethylamine → HCID 11508173、化合物

HRID 735241ノート

反応式

HRID 735241 の反応式
[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

参加物

6

反応物 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 11638332HCID 11638332、化合物

生成物 1

HCID 11508173HCID 11508173、化合物収率 65.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b3ed995d4991413093fdde097db76e32
出典データセット
uspto-grants-2009_09
特許番号
US07592457B2

反応ノート

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