Methyl iodide → 5,10-Dimethyl-5,10-dihydrobenzo(a)phenazine

HRID 376555

Reaction equation

HRID 376555 reaction equation
[CH:1]1[C:6]2=[C:7]3[C:16](=[CH:17][CH:18]=[C:5]2C=[CH:3][CH:2]=1)[N:15]=[C:14]1[C:9]([CH:10]=[CH:11][CH:12]=[CH:13]1)=[N:8]3.[K].[Na].I[CH3:22].[CH2:23]([CH2:26]OC)OC>>[CH3:5][CH:18]1[CH:17]=[C:16]2[C:7](=[N:8][C:9]3[C:14](=[N:15]2)[CH:13]=[CH:12][CH:11]([CH3:22])[CH:10]=3)[C:6]2[CH:1]=[CH:2][CH:3]=[CH:23][C:26]1=2

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 80711,2-DimethoxyethaneHCID 136045Benzo(A)PhenazineHCID 16211683Potassium alloy, nonbase, K,Na

Product 1

HCID 220553625,10-Dimethyl-5,10-dihydrobenzo(a)phenazine

Procedure

This phenazine was reduced with a 3:1 potassium/sodium metal alloy in dimethoxyethane, to the brick red alkali metal adduct. Alkylation occurred over 1 hour with addition of iodomethane. Residual K/Na alloy was quenched with addition of ethanol. The product was isolated with column chromatography and was recrystallized from ethylacetate/hexane. 2.0 grams of product was isolated for a 38% overall yield.

Workup

  1. customResidual K/Na alloy was quenched with addition of ethanol
  2. customThe product was isolated with column chromatography
  3. customwas recrystallized from ethylacetate/hexane

Sources & evidence

ORD record
ord-cf2a1a7bd08145b3b9e3448a24871c89
Source dataset
uspto-grants-2000_02
Patent number
US06020987

Linked notes

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