Isopropanol → 5,7-Dimethyl-imidazo[1,2-f]phenanthridine

HRID 606691

Reaction equation

HRID 606691 reaction equation
C[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11]([CH:12]([NH2:17])[N:13](C)[C:14]=2[CH:15]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3.[C:18](Cl)(=O)C.C(=O)(O)[O-].[Na+].C(Cl)Cl.[CH:30](O)([CH3:32])[CH3:31]>O>[CH3:31][C:30]1[C:32]2[N:13]3[CH:14]=[CH:15][N:17]=[C:12]3[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]=2[CH:4]=[C:3]([CH3:2])[CH:18]=1

Participants

7

Reactant 5

HCID 3776IsopropanolHCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 574535493,5-Dimethyl-6-phenanthridinamine

Product 1

HCID 581626885,7-Dimethyl-imidazo[1,2-f]phenanthridineYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3,5-Dimethyl-6-phenanthridinamine (8.6 g, 39 mmol), a 50% solution of acetyl chloride (4.6 g, 58 mmol) in water, sodium bicarbonate (6.5 g, 77.4 mmol) in 258 mL of isopropyl alcohol were heated to reflux for 40 hours. After cooling the crude product was dissolve into methylene chloride and vacuum filtered. The filtrate was concentrated and the crude product was crystallized in methylene chloride and ethyl acetate mixture. The pure product was collected by vacuum filtration to give 5,7-dimethyl-imidazo[1,2-f]phenanthridine) (3.8 g, 40% yield) as determined by NMR.

Workup

  1. temperatureto reflux for 40 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customthe crude product was crystallized in methylene chloride
  5. filtrationThe pure product was collected by vacuum filtration

Sources & evidence

ORD record
ord-e346abd48edf4982b01697afad525d43
Source dataset
uspto-grants-2011_03
Patent number
US07915415B2

Linked notes

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