Acetic Anhydride → N-(Phenazin-1-yl)acetamide

HRID 41806Notes

Reaction equation

HRID 41806 reaction equation
[NH2:1][C:2]1[C:15]2[C:6](=[N:7][C:8]3[C:13]([N:14]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:5]=[CH:4][CH:3]=1.[C:16](OC(=O)C)(=[O:18])[CH3:17]>C(O)(=O)C>[C:16]([NH:1][C:2]1[C:15]2[C:6](=[N:7][C:8]3[C:13]([N:14]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:5]=[CH:4][CH:3]=1)(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 761381-Aminophenazine

Product 1

HCID 57896198N-(Phenazin-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Scheme 8 provides a synthetic route to a 1-acetamido-N-ethyl phenazine derivative (35). A 3-amino-catechol hydrochloride (30) is reacted with silver oxide and anhydrous sodium sulfate in ethyl acetate to give 3-amino-1,2-quinone (31), which is further reacted in situ with ortho phenylenediamine (32) to give 1-amino phenazine (33). The amino phenazine (33) is acetylated with acetic anhydride in acetic acid to give 1-acetamido phenazine (34). The resulting 1-acetamido phenazine is reacted with diethyl sulfate in the presence of potassium carbonate to give N-ethyl-1-acetamido-phenazine (35).

Sources & evidence

ORD record
ord-a44dffd78eeb485284484700dd580e32
Source dataset
uspto-grants-2013_09
Patent number
US08535511B2

Reaction notes

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