4-Methylmorpholine → N,N-dihexyl-1,2-dihydro-2-oxoquinoline-3-carboxamide

HRID 2269618

反応式

HRID 2269618 の反応式
[O:1]=[C:2]1[C:11]([C:12]([OH:14])=O)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.CN1CCOCC1.C(Cl)(=O)OCC(C)C.[CH2:30]([NH:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>O1CCCC1.CN(C)C=O>[CH2:37]([N:36]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:12]([C:11]1[C:2](=[O:1])[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:14])[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 8920DihexylamineHCID 62365Isobutyl chloroformateHCID 3324882-Quinolone-3-carboxylic acid

生成物 1

HCID 15461775N,N-dihexyl-1,2-dihydro-2-oxoquinoline-3-carboxamide収率 75.8%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-15 °C

実験手順

In a mixture of 50 ml of tetrahydrofuran and 250 ml of N,N-dimethylformamide were dissolved 9.46 g of 1,2-dihydro-2-oxoquinoline-3-carboxylic acid and 5.06 g of N-methylmorpholine, and after cooling to −15° C., 6.83 g of isobutyl chlorocarbonate was added dropwise over 10 minutes. After stirring at −15° C. for 10 minutes, 9.73 g of dihexylamine was added dropwise over 5 minutes. After stirring at −15° C. for 4 hours and then at room temperature overnight, the reaction mixture was concentrated under reduced pressure, and the residue, after addition of ethyl acetate, was washed with water, 1N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure. The residue was recrystallized from hexane to give 13.51 g of N,N-dihexyl-1,2-dihydro-2-oxoquinoline-3-carboxamide.

後処理

  1. stirringAfter stirring at −15° C. for 4 hours
  2. concentrationat room temperature overnight, the reaction mixture was concentrated under reduced pressure
  3. additionthe residue, after addition of ethyl acetate
  4. washwas washed with water, 1N hydrochloric acid
  5. dry with materiala saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
  6. customAfter removal of the drying agent
  7. filtrationby filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was recrystallized from hexane

出典と根拠

ORDレコード
ord-29bf628c2e574a03b0bbbdf8a4b778be
出典データセット
uspto-grants-2001_12
特許番号
US06329525B1

関連ノート

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