Hydrochloric Acid → 4-(2-(3,4-Dihydro-6,7-dimethoxy-2(1H)-isoquinolinyl)ethyl)benzenamine

HRID 1192844ノート

反応式

HRID 1192844 の反応式
Cl.C(O)C.[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[CH2:13][N:12]([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=1)[CH2:11][CH2:10]2.[OH-].[Na+]>[Fe].O.ClCCl.C(Cl)(Cl)Cl.CO>[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[CH2:13][N:12]([CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([NH2:27])=[CH:25][CH:26]=1)[CH2:11][CH2:10]2

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 104274766,7-Dimethoxy-2-[2-(4-nitrophenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline

生成物 1

HCID 100412274-(2-(3,4-Dihydro-6,7-dimethoxy-2(1H)-isoquinolinyl)ethyl)benzenamine収率 90%

試薬・触媒・溶媒 4

HCID 23925Iron触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 21584188Chloroform methanol溶媒

反応条件

温度
80 °C

実験手順

Iron (1.27 kg, 23.48 mol), hydrochloric acid (127 mL, 1.54 mol) and 6.7 L of 50% aqueous ethanol were added to a reactor, and stirred for 1 hour at 80° C. 6,7-dimethoxy-2-(4-nitrophenethyl)-1,2,3,4-tetrahydroisoquinoline (1.3 kg, 3.91 mol) obtained in Step 1-1 was slowly added thereto for one hour, followed by stirring for 3 hours at 80° C. After checking completion of the reaction by thin layer chromatography (eluent: chloroform/methanol=15/1), the reaction mixture was cooled to room temperature. 5.3 L of dichloromethane and 5.3 L of water were added thereto, the reaction mixture was neutralized by adding 804 mL of 10% aqueous sodium hydroxide. The resulting mixture was filtered through a Celite pad and washed with 3 L of methylenechloride. The organic layer was collected, dried over magnesium sulfate, and then filtered. The solvent was removed under reduced pressure, and dried with hot air at 40° C. in an oven to obtain the title compound (1.05 kg, 90%).

後処理

  1. waitfor one hour
  2. stirringby stirring for 3 hours at 80° C
  3. temperaturethe reaction mixture was cooled to room temperature
  4. filtrationThe resulting mixture was filtered through a Celite pad
  5. washwashed with 3 L of methylenechloride
  6. customThe organic layer was collected
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customThe solvent was removed under reduced pressure
  10. customdried with hot air at 40° C. in an oven

出典と根拠

ORDレコード
ord-c91960c4ba274f3996983cec5ccbe8db
出典データセット
uspto-grants-2014_03
特許番号
US08680277B2

反応ノート

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