Phenazine → 2,3-dimethylbenzo(B)phenazine

HRID 610778

Reaction equation

HRID 610778 reaction equation
[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[CH3:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17](=O)[C:16](=O)[CH:15]=1.C1C2C(=NC3C(N=2)=CC=CC=3)C=CC=1.IC>C(O)(=O)C.C(O)C>[CH3:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]2[N:1]=[C:2]3[C:11](=[N:12][C:16]=2[CH:15]=1)[CH:10]=[C:9]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=[CH:3]3

Participants

7

Reactant 4

HCID 4757PhenazineHCID 6328Methyl iodideHCID 698722,3-DiaminonaphthaleneHCID 122947044,5-Dimethyl-1,2-benzoquinone

Product 1

HCID 193501462,3-dimethylbenzo(B)phenazine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

The 2,3-dimethylbenzo(B)phenazine was prepared by the condensation of 2,3-diaminonapthalene with 4,5-dimethyl-1,2-benzoquinone in 4:1 ethanol to acetic acid at reflux for 2 hours. The phenazine was alkylated by the procedure of Synthesis Example 8, using iodomethane. Electrochemical analysis was consistent with an N,N'-dialkylated phenazine.

Workup

  1. temperatureat reflux for 2 hours

Sources & evidence

ORD record
ord-38d5154dd9e94c729f7719601216679e
Source dataset
uspto-grants-1999_12
Patent number
US05998617

Linked notes

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