1,4-Naphthoquinone → 1-Octyl-2,5-bis(1,4-naphthoquinon-2-yl)pyrrole

HRID 376746Notes

Reaction equation

HRID 376746 reaction equation
[C:1]1(=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH:3]=[CH:2]1.[CH2:13]([N:21]1[CH:25]=[CH:24][CH:23]=[CH:22]1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>C(O)(=O)C>[CH2:13]([N:21]1[C:22]([C:3]2[C:4](=[O:11])[C:5]3[C:10]([C:1](=[O:12])[CH:2]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:23][CH:24]=[C:25]1[C:3]1[C:4](=[O:11])[C:5]2[C:10]([C:1](=[O:12])[CH:2]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 85301,4-NaphthoquinoneHCID 106312041-n-Octylpyrrole

Product 1

HCID 106964481-Octyl-2,5-bis(1,4-naphthoquinon-2-yl)pyrroleYield 49%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The same procedure as in Example 7 was followed by stirring 10 millimol of 1,4-naphthoquinone with 2.5 millimol of N-octylpyrrole in 40 ml of acetic acid at 50° C. for 5 hours. The 1-octyl-2,5-bis(1,4-naphthoquinon-2-yl)pyrrole was thus obtained in a yield of 49% after chromatography on a column of silica.

Sources & evidence

ORD record
ord-5d302221676f432e8d75c6940b068c5e
Source dataset
uspto-grants-2000_02
Patent number
US06022379

Reaction notes

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