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

HRID 716591

Reaction equation

HRID 716591 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(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.

Workup

  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

Sources & evidence

ORD record
ord-87dd13e73e4f40b6a8134ba00e85ebdf
Source dataset
uspto-grants-2015_11
Patent number
US09190621B2

Linked notes

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