Hydrochloric Acid → HCID 53644723, compound

HRID 1459669Notes

Reaction equation

HRID 1459669 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[N+:5]([C:8]1[C:21]2[NH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=O)[C:12]=2[CH:11]=[CH:10][CH:9]=1)([O-:7])=[O:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[N+:5]([C:8]1[C:21]2[NH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][C:12]=2[CH:11]=[CH:10][CH:9]=1)([O-:7])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2326414-nitroacridin-9(10h)-oneHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 53644723HCID 53644723, compoundYield 13.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.361 g (10 mmol) of aluminum chloride was dissolved in 10 ml of dry tetrahydrofuran. To the solution thus obtained was slowly added 75 ml of a solution of 1.201 g (5 mmol) of 4-nitro-9(10H)-acridinone in dry tetrahydrofuran. After stirring at room temperature for 30 minutes, 759 mg (20 mmol) of lithium aluminum hydride was added thereto in portions. After stirring at room temperature for 30 minutes and then at 55° C. for additional 30 minutes, the reaction mixture was cooled to room temperature and 5 ml of 1N hydrochloric acid was added thereto. After concentrating, ethyl acetate and water were added to the residue and the formed insoluble matters were filtered off. The organic layer was separated from the filtrate and dried over magnesium sulfate. After concentrating, the residue was purified by silica gel column chromatography. Thus 148 mg of the title compound was obtained.

Workup

  1. customTo the solution thus obtained
  2. stirringAfter stirring at room temperature for 30 minutes
  3. waitat 55° C. for additional 30 minutes
  4. temperaturethe reaction mixture was cooled to room temperature
  5. concentrationAfter concentrating
  6. additionethyl acetate and water were added to the residue
  7. filtrationthe formed insoluble matters were filtered off
  8. customThe organic layer was separated from the filtrate
  9. dry with materialdried over magnesium sulfate
  10. concentrationAfter concentrating
  11. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5d8cba3226a1497bbc9e25c65328dd2a
Source dataset
uspto-grants-1998_12
Patent number
US05854274

Reaction notes

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