Ethyl Acetate → Acridine, 1,9-diamino-

HRID 2275511Notes

Reaction equation

HRID 2275511 reaction equation
[N+:1]([C:4]1[C:17]2[C:8](=[N:9][C:10]3[C:15]([C:16]=2[NH2:18])=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:7]=[CH:6][CH:5]=1)([O-])=O.C(OCC)(=O)C.C([O-])=O.[NH4+]>CO>[NH2:1][C:4]1[C:17]2[C:8](=[N:9][C:10]3[C:15]([C:16]=2[NH2:18])=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 1467091-Nitro-9-aminoacridineHCID 2723923Ammonium formate2×

Product 1

HCID 31623Acridine, 1,9-diamino-Yield 40.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 50 mL rbf equipped with a nitrogen bubbler were charged 1-nitro-9-aminoacridine (162 mg, 0.68 mmol) and ethyl acetate (3.4 mL). Methanol (1.7 mL) and Pd/Alumina 10% (22 mg) were added and the reaction mixture was stirred to a fine suspension. Ammonium formate (85 mg, 1.35 mmol) was added and the mixture was stirred for 20 min at room temperature. A further portion of ammonium formate (128 mg, 2.03 mmol) was then added. Stirring was maintained overnight. The reaction mixture was filtered to remove catalyst and concentrated to dryness. The residue was purified by flashmaster column eluting with a gradient elution (DCM→DCM:MeOH 98:2) to afford pure 1,9-diaminoacridine as a brown-yellow solid (57 mg, 40%). 1H NMR and LCMS analyses conformed to structure.

Workup

  1. customTo a 50 mL rbf equipped with a nitrogen bubbler
  2. stirringthe mixture was stirred for 20 min at room temperature
  3. stirringStirring
  4. temperaturewas maintained overnight
  5. filtrationThe reaction mixture was filtered
  6. customto remove catalyst
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by flashmaster column
  9. washeluting with a gradient elution (DCM→DCM:MeOH 98:2)

Sources & evidence

ORD record
ord-44cfd1ec72974077914e63b9e341ab24
Source dataset
uspto-grants-2015_09
Patent number
US09127164B2

Reaction notes

Loading…