Potassium Hydroxide → 8-Chloro-2,4-dimethyl-5,6-dihydrobenzo[c]acridine

HRID 716591

반응식

HRID 716591 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9]O.[CH3:11][C:12]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]2[C:13]=1[CH2:14][CH2:15][CH2:16][C:17]2=O.[OH-].[K+]>C1(C)C=CC=CC=1>[Cl:8][C:4]1[C:3]2[C:2](=[N:1][C:17]3[C:18]4[CH:19]=[C:20]([CH3:22])[CH:21]=[C:12]([CH3:11])[C:13]=4[CH2:14][CH2:15][C:16]=3[CH:9]=2)[CH:7]=[CH:6][CH:5]=1

참가 물질

5

반응물 3

HCID 14797Potassium HydroxideHCID 836193,4-dihydro-5,7-dimethylnaphthalen-1(2H)-oneHCID 21925574(2-Amino-6-chlorophenyl)methanol

생성물 1

HCID 712451148-Chloro-2,4-dimethyl-5,6-dihydrobenzo[c]acridine수율 67.4%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

(2-Amino-6-chlorophenyl)methanol (16 g, 101 mmol), 5,7-dimethyl-3,4-dihydronaphthalen-1(2H)-one (20.0 g, 111 mmol), RuCl2(PPh3)3 (0.971 g, 1.01 mmol), and KOH (5.7 g, 101 mmol) were refluxed in 200 mL of toluene for 12 h. Water was collected from the reaction using a Dean-stark trap. The reaction mixture was allowed to cool to room temperature and filtered through a silica gel plug and eluted with dichloromethane. The product was washed by methanol and recrystallized from hexane to obtain ˜20 gram of the desired product which was confirmed by GC-MS.

후처리

  1. customWater was collected from the reaction
  2. filtrationfiltered through a silica gel plug
  3. washeluted with dichloromethane
  4. washThe product was washed by methanol
  5. customrecrystallized from hexane

출처 및 근거

ORD 기록
ord-87dd13e73e4f40b6a8134ba00e85ebdf
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09190621B2

연결된 노트

불러오는 중…