Hydrochloric Acid → 1-(4-chlorobutyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine

HRID 1360554

反応式

HRID 1360554 の反応式
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10]([C:22]#[N:23])=[N:11][N:12]([CH2:19][CH2:20][CH3:21])[C:13]=1[CH2:14][CH2:15][CH2:16][CH2:17][Cl:18]>C(O)C>[Cl:18][CH2:17][CH2:16][CH2:15][CH2:14][C:13]1[N:12]([CH2:19][CH2:20][CH3:21])[N:11]=[C:10]2[C:9]=1[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[N:2]=[C:22]2[NH2:23]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 669588824-(2-aminophenyl)-5-(4-chlorobutyl)-1-propyl-1H-pyrazole-3-carbonitrile

生成物 1

HCID 577175341-(4-chlorobutyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine収率 63.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

Hydrochloric acid (18 mL, 71.0 mmol) in ethanol was added dropwise to a solution of 4-(2-aminophenyl)-5-(4-chlorobutyl)-1-propyl-1H-pyrazole-3-carbonitrile (7.50 g, 23.7 mmol) in 150 mL of ethanol. The resultant solution was heated to reflux overnight, concentrated under reduced pressure, and diluted with water. The pH of the mixture was adjusted to 9-10 by slow addition of solid sodium carbonate. The aqueous layer was extracted with several portions of dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford a reddish solid. The material was purified via flash column chromatography on silica gel (eluting with a 96:4 mixture of dichloromethane/methanol) to afford 4.78 g of 1-(4-chlorobutyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine.

後処理

  1. temperatureto reflux overnight
  2. concentrationconcentrated under reduced pressure
  3. additiondiluted with water
  4. additionThe pH of the mixture was adjusted to 9-10 by slow addition of solid sodium carbonate
  5. extractionThe aqueous layer was extracted with several portions of dichloromethane
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto afford a reddish solid
  11. customThe material was purified via flash column chromatography on silica gel (
  12. washeluting with a 96:4 mixture of dichloromethane/methanol)

出典と根拠

ORDレコード
ord-406860c1a3494857b8df1203262b0dff
出典データセット
uspto-grants-2011_02
特許番号
US07879849B2

関連ノート

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