Di-tert-butyl peroxide → 2,9-Di-t-butylphenanthridinone

HRID 2363777Notes

Reaction equation

HRID 2363777 reaction equation
[CH:1]([NH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:15]=1)=O.C([O:28]OC(C)(C)C)(C)(C)C>ClC1C=CC=CC=1>[C:10]([CH:7]1[CH:8]=[CH:9][C:4]2[C:5](=[C:14]3[C:19](=[CH:1][N:3]=2)[CH:18]=[CH:17][C:16]([C:20]([CH3:21])([CH3:22])[CH3:23])=[CH:15]3)[C:6]1=[O:28])([CH3:12])([CH3:11])[CH3:13]

Participants

4

Reactant 2

HCID 8033Di-tert-butyl peroxideHCID 86614227N-formyl-2-amino-3',5-di-t-butyl biphenyl

Product 1

HCID 668135942,9-Di-t-butylphenanthridinone

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
110 °C

Procedure

The above compound, N-formyl-2-amino-3′,5-di-t-butyl biphenyl (6.5 g, 21 mmol) was dissolved into 50 mL of chlorobenzene to which 5 equivalents of di-t-butyl peroxide was added. The reaction mixture was heated to 110° C. for 72 hours. The reaction mixture was concentrated in half and cooled to 0° C. The precipitate that formed was collected by vacuum filtration. The off-white solid was washed with hexanes to give 2,9-di-tert-butylphenanthridinone as determined by GCMS and not purified any further.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated in half
  3. temperaturecooled to 0° C
  4. customThe precipitate that formed
  5. filtrationwas collected by vacuum filtration
  6. washThe off-white solid was washed with hexanes

Sources & evidence

ORD record
ord-5f220b8e0af241df8cb6a32abef6db1f
Source dataset
uspto-grants-2014_04
Patent number
US08691988B2

Reaction notes

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