Aminoacetaldehyde dimethyl acetal → 7,10-Di-tert-butyl-imidazo[1,2-f]phenanthridine

HRID 1618460Notes

Reaction equation

HRID 1618460 reaction equation
[C:1]([C:5]1[CH:18]=[CH:17][C:16]2[C:7](=[C:8]3[C:13](=[C:14](Cl)[N:15]=2)[CH:12]=[CH:11][C:10]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:9]3)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CO[CH:26](OC)[CH2:27][NH2:28]>COCCOCCOC>[C:1]([C:5]1[CH:18]=[CH:17][C:16]2[N:15]3[CH:26]=[CH:27][N:28]=[C:14]3[C:13]3[CH:12]=[CH:11][C:10]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:9][C:8]=3[C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 574376592,9-Di-tert-butyl-6-chlorophenanthridine

Product 1

HCID 581623657,10-Di-tert-butyl-imidazo[1,2-f]phenanthridineYield 56%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

2,9-Di-t-butyl-6-chlorophenanthridine (3.7 grams, 11.0 mmole) was added to a reaction flask containing aminoacetaldehyde dimethylacetal (2.4 grams, 23 mmole) dissolved into 200 mL of diglyme, heated to reflux and stirred under a nitrogen atmosphere. After 96 hours the reaction was complete as determined by TLC. The reaction mixture was cooled to room temperature and the excess solvent removed by distillation. The residue was taken up into methylene chloride. The solvent was dried over magnesium sulfate filtered and concentrated. The crude product was purified by silica gel chromatography using 10% ethyl acetate and 90% methylene chloride as the eluents. The purified product was collected, washed with hexanes, and dried to give 7,10-di-tert-butyl-imidazo[1,2-f]phenanthridine (2.0 grams, 56% yield) as a white solid.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. customthe excess solvent removed by distillation
  4. dry with materialThe solvent was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel chromatography
  8. customThe purified product was collected
  9. washwashed with hexanes
  10. customdried

Sources & evidence

ORD record
ord-150a047850d04c64a1f7e28356404557
Source dataset
uspto-grants-2014_07
Patent number
US08766529B2

Reaction notes

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