Hydrochloric Acid → 10,10-Dimethyl-8,9,10,11-tetrahydro-3,8,11-triaza-benzo[a]fluoren-7-one

HRID 2066919Notes

Reaction equation

HRID 2066919 reaction equation
C(=N[NH:15][C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][N:20]=[CH:21]2)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:26][C:27]1([CH3:35])[CH2:32][NH:31][C:30](=[O:33])[CH2:29][C:28]1=O.[OH-].[Na+].Cl>C(O)(=O)C.O.CO>[CH3:26][C:27]1([CH3:35])[C:28]2[NH:15][C:16]3[C:25](=[CH:24][CH:23]=[C:22]4[CH:21]=[N:20][CH:19]=[CH:18][C:17]4=3)[C:29]=2[C:30](=[O:33])[NH:31][CH2:32]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 251938265,5-Dimethylpiperidine-2,4-dioneHCID 59226081N-benzhydrylidene-N'-isoquinolin-5-yl-hydrazine

Product 1

HCID 2499408210,10-Dimethyl-8,9,10,11-tetrahydro-3,8,11-triaza-benzo[a]fluoren-7-oneYield 56.5%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

A mixture of N-benzhydrylidene-N′-isoquinolin-5-yl-hydrazine (154 mg, 0.48 mmol) and 5,5-dimethylpiperidine-2,4-dione (98 mg, 0.69 mmol), dissolved in acetic acid (2 mL) and water (8 drops), was submitted to microwaves for 40 minutes at 150° C. The mixture was treated with concentrated NaOH to pH 9 and was extracted three times with ethyl acetate. Purification by flash chromatography of the concentrated residue, with dichloromethane/methanol/acetic acid/water 30/2/0.5/0.2→30/4/1/0.5 as eluant, afforded a solid product, which was dissolved in methanol and treated with 1.25M HCl in methanol to pH 1. The solvent was removed under vacuum and the residue was treated with diethylether. The resulting solid was filtered, washed with diethylether, and dried under vacuum, affording 72 mg of the title compound as hydrochloric salt (28%).

Workup

  1. extractionwas extracted three times with ethyl acetate
  2. customPurification by flash chromatography of the concentrated residue
  3. customwith dichloromethane/methanol/acetic acid/water 30/2/0.5/0.2→30/4/1/0.5 as eluant, afforded a solid product, which
  4. customThe solvent was removed under vacuum
  5. additionthe residue was treated with diethylether
  6. filtrationThe resulting solid was filtered
  7. washwashed with diethylether
  8. customdried under vacuum

Sources & evidence

ORD record
ord-e8635543b36e4e6e91406354fdbddb2a
Source dataset
uspto-grants-2012_10
Patent number
US08293762B2

Reaction notes

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