Hydrochloric Acid → 2-Methyl-N-[4-[(5(6H)-phenanthridinyl)carbonyl]phenyl]benzamide

HRID 1938260Notes

Reaction equation

HRID 1938260 reaction equation
[CH:1]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:15][C:16]1[CH:33]=[CH:32][CH:31]=[CH:30][C:17]=1[C:18]([NH:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1)=[O:19].Cl>N1C=CC=CC=1>[CH3:15][C:16]1[CH:33]=[CH:32][CH:31]=[CH:30][C:17]=1[C:18]([NH:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([N:6]2[CH2:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]2=3)=[O:26])=[CH:23][CH:22]=1)=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2199665,6-DihydrophenanthridineHCID 107074414-[(2-methylbenzoyl)amino]benzoyl Chloride

Product 1

HCID 153079712-Methyl-N-[4-[(5(6H)-phenanthridinyl)carbonyl]phenyl]benzamideYield 18.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 0.181 g (1.0 mmol) of 5,6-dihydrophenanthridine in 2 ml of warm pyridine is added 0.273 g (1.0 mmol) of 4-[(2-methylbenzoyl)amino]-benzoyl chloride. The mixture is stirred overnight at room temperature, 1.2 ml of 2N HCl added. The solid which separates is filtered and washed with water. The solid is dissolved in dichloromethane and the solution washed with 2M sodium carbonate. The organic layer is concentrated and the residue chromatographed twice on silica gel with ethyl acetate-hexane as solvent to give 79 mg of crystals, m.p. 190°-194° C. Mass Spec-FAB 419 (M+R). Anal. Calc'd for C28H20N2O2H2O: C,77.4; H,5.1; N,6.4. Found: C,77.5; H,5.1; N,6.4.

Workup

  1. filtrationThe solid which separates is filtered
  2. washwashed with water
  3. dissolutionThe solid is dissolved in dichloromethane
  4. washthe solution washed with 2M sodium carbonate
  5. concentrationThe organic layer is concentrated
  6. customthe residue chromatographed twice on silica gel with ethyl acetate-hexane as solvent

Sources & evidence

ORD record
ord-54282cda5a864d1eaedda11c6aa71846
Source dataset
uspto-grants-1997_12
Patent number
US05693635

Reaction notes

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