Potassium Carbonate → 5-Phenyl-5,6-dihydrophenanthridine

HRID 523446Notes

Reaction equation

HRID 523446 reaction equation
Br[C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Br-].C([N+](C)(C)C)C1C=CC=CC=1.CC(O)=O.CC(O)=O.[Pd]>[C:6]1([N:5]2[CH2:4][C:3]3[C:18](=[CH:19][CH:20]=[CH:21][CH:2]=3)[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]2=3)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 85712531(2-Bromobenzyl)diphenylamine

Product 1

HCID 143377485-Phenyl-5,6-dihydrophenanthridine

Reagents, catalysts & solvents 3

HCID 21449Benzyltrimethylammonium bromideCatalystHCID 4144353Palladium (II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

10 g (0.295 mol) of (2-bromobenzyl)diphenylamine are dissolved in 500 ml of dimethylformamide under protective atmosphere. 3.4 g (0.075 mol) of benzyltrimethylammonium bromide and 6.1 g (0.443 mol) of potassium carbonate are added to this solution. 0.99 g (0.004 mol) of Pd(OAC)2 is subsequently added under protective gas, and the mixture is stirred at 120° C. for 9 h. After this time, the reaction mixture is cooled to room temperature and extracted with dichloromethane. The combined organic phases are dried over Na2SO4 and evaporated. The residue is recrystallised from n-heptane. The yield is 6 g (80%).

Workup

  1. temperatureAfter this time, the reaction mixture is cooled to room temperature
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic phases are dried over Na2SO4
  4. customevaporated
  5. customThe residue is recrystallised from n-heptane

Sources & evidence

ORD record
ord-495a6adf76a44be8ab73ccc2176b0f05
Source dataset
uspto-grants-2016_05
Patent number
US09337430B2

Reaction notes

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