2,5-Dimethoxy-4-benzoquinone → HCID 19710467, compound

HRID 726163Notes

Reaction equation

HRID 726163 reaction equation
[CH2:1]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH2:12])[CH2:2][CH2:3][CH3:4].CO[C:15]1[C:16](=O)[CH:17]=[C:18](OC)[C:19](=O)[CH:20]=1>C(O)(=O)C>[CH2:1]([N:5]1[C:18]2[C:19]([CH:20]=[C:15]3[C:16]([CH:17]=2)=[N:12][C:7]2[C:6](=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]3[CH2:1][CH2:2][CH2:3][CH3:4])=[N:12][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]1=2)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 1014052,5-Dimethoxy-4-benzoquinoneHCID 11228985N1-Butylbenzene-1,2-diamine

Product 1

HCID 19710467HCID 19710467, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.65 g (10 mmol) N-butyl-2-aminoaniline and 0.84 g (5 mmol) 2,5-dimethoxybenzoquinone i 50 ml glacial acetic acid are heated to boiling under reflux for three hours followed by evaporation to dryness. The darkblue powder is treated with 50 ml 10% ammonia solution and washed thoroughly with water, ethanol, and acetone (10 ml). After a thorough drying under vacuum, 1.95 g (95%) 5,12-dibutyl-5,12-dihydro-5,7,12,14-tetraazapentacene is obtained.

Workup

  1. temperatureunder reflux for three hours
  2. customfollowed by evaporation to dryness
  3. additionThe darkblue powder is treated with 50 ml 10% ammonia solution
  4. washwashed thoroughly with water, ethanol, and acetone (10 ml)
  5. customAfter a thorough drying under vacuum

Sources & evidence

ORD record
ord-00f70e8d8aac47458128c673a842fb61
Source dataset
uspto-grants-1998_01
Patent number
US05708123

Reaction notes

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