2-Nitroanisole → HCID 20248128, compound

HRID 1589137Notes

Reaction equation

HRID 1589137 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([CH3:10])[CH:4]=1.[CH3:11][O:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=1[N+:19]([O-])=O.[OH-].[K+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:10])[C:6]2[C:8]([CH:9]=1)=[N:19][C:18]1[C:17](=[CH:16][CH:15]=[CH:14][C:13]=1[O:12][CH3:11])[N:7]=2

Participants

5

Reactant 3

HCID 70482-NitroanisoleHCID 76102-Methyl-4-methoxyanilineHCID 14797Potassium Hydroxide

Product 1

HCID 20248128HCID 20248128, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mechanically stirred mixture of 66.0 ml (0.51 mol) of freshly distilled 4-methoxy-2-methylaniline, 50.5 ml (0.41 mol) of freshly distilled o-nitroanisole, 189 g (3.37 mol) of finely powdered potassium hydroxide, and 945 ml of toluene was heated to reflux (initially exothermic) for 1 hour. The mixture was then cooled to room temperature, filtered, and the filter cake washed with toluene, 1% methanol/dichloromethane, and dichloromethane. The solvent from the combined filtrate and washings was removed in vacuo to yield 86 g of black solid. The black material was then flash filtered through silica gel eluting with ether and the fractions containing the desired phenazine (Rf =0.22 on silica gel, dichloromethane) were combined, concentrated in vacuo and purified by flash chromatography, eluting with dichloromethane. A final chromatography on a Waters Prep-500 chromatograph (6:1 hexane-acetone) followed by recrystallization from a hexane/toluene mixture afforded 12.3 g of the title compound as yellow needles, melting point 201°-202° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux (initially exothermic) for 1 hour
  3. filtrationfiltered
  4. washthe filter cake washed with toluene, 1% methanol/dichloromethane, and dichloromethane
  5. customThe solvent from the combined filtrate and washings was removed in vacuo

Sources & evidence

ORD record
ord-f0ad39dc63964aaaa5ec8421c129975b
Source dataset
uspto-grants-1986_02
Patent number
US04568675

Reaction notes

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