Sodium Hydroxide → 6-Methylphenanthridine

HRID 718737Notes

Reaction equation

HRID 718737 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=O)[CH3:9].[OH-].[Na+]>>[CH3:9][C:8]1[N:7]=[C:2]2[C:1](=[C:11]3[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]3)[CH:6]=[CH:5][CH:4]=[CH:3]2

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 164472-Acetamidobiphenyl

Product 1

HCID 3179886-MethylphenanthridineYield 86.6%

Conditions

Temperature
150 °C

Procedure

A mixture of the acetamide 4 (717 mg, 3.39 mmol) and finely grinded polyphosphoric acid (10 mL, 115% H3PO4 equiv.) was stirred at 150° C. for 2.5 hours. The reaction mixture was then cooled to 0° C. and slowly basified to pH 14 with saturated NaOH (aq). The mixture was extracted with CH2Cl2 (4×30 mL), and the organic phase dried with MgSO4. Evaporation of the solvent under reduced pressure, followed by flash chromatography over silica, eluting with a gradient of 100% CH2Cl2 to 10% MeOH/90% CH2Cl2, yielded the phenanthridine 5 as a crystalline white solid (567 mg, 86.6%).

Workup

  1. extractionThe mixture was extracted with CH2Cl2 (4×30 mL)
  2. dry with materialthe organic phase dried with MgSO4
  3. customEvaporation of the solvent under reduced pressure
  4. washeluting with a gradient of 100% CH2Cl2 to 10% MeOH/90% CH2Cl2

Sources & evidence

ORD record
ord-34762dc12599431c93c1d3850fd542a6
Source dataset
uspto-grants-2015_11
Patent number
US09194802B2

Reaction notes

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