Triethylamine → HCID 57447109、化合物

HRID 2366718ノート

反応式

HRID 2366718 の反応式
C(N(CC)CC)C.[NH2:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[Cl:19])=[CH:16][CH:15]=[CH:14][CH:13]=2.[C:20](Cl)(=[O:24])[CH2:21][CH2:22][CH3:23].C(=O)(O)[O-].[Na+]>ClCCl.CO>[Cl:19][C:18]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][C:9]=1[NH:8][C:20](=[O:24])[CH2:21][CH2:22][CH3:23]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 516892Sodium BicarbonateHCID 8173324-chloroquinolin-3-amine

生成物 1

HCID 57447109HCID 57447109、化合物

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

Triethylamine (22.3 mL, 0.160 mmol) was added with stirring to a solution of 3-amino-4-chloroquinoline, see Surrey et al., Journal of the American Chemical Society, 73, pp. 2413-2416 (1951), (13.2 g, 74.0 mmol) in anhydrous dichloromethane (100 mL). A solution of butyryl chloride (13 mL, 125 mmol) in dichloromethane (50 mL) was then added dropwise, and the reaction mixture was stirred at ambient temperature overnight. Methanol (25 mL) was added, and the reaction mixture was stirred for one hour at ambient temperature. Saturated aqueous sodium bicarbonate (50 mL) was added, and the resulting mixture was stirred at ambient temperature for 30 minutes and then allowed to stand. The aqueous layer was separated and extracted with dichloromethane (75 mL), and the combined organic fractions were then washed with saturated aqueous sodium bicarbonate (2×50 mL), dried over potassium carbonate, filtered, and concentrated under reduced pressure. The crude product (22.8 g) was recrystallized from a mixture of toluene (45 mL) and hexane (15 mL) to provide 9.2 of N-(4-chloroquinolin-3-yl)butanamide as brown needles.

後処理

  1. stirringthe reaction mixture was stirred for one hour at ambient temperature
  2. stirringthe resulting mixture was stirred at ambient temperature for 30 minutes
  3. customThe aqueous layer was separated
  4. extractionextracted with dichloromethane (75 mL)
  5. washthe combined organic fractions were then washed with saturated aqueous sodium bicarbonate (2×50 mL)
  6. dry with materialdried over potassium carbonate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product (22.8 g) was recrystallized from a mixture of toluene (45 mL) and hexane (15 mL)

出典と根拠

ORDレコード
ord-d3388ee2a8474918974c916ff9c2f602
出典データセット
uspto-grants-2014_04
特許番号
US08697873B2

反応ノート

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