Methanol → HCID 86634099, compound

HRID 2275510Notes

Reaction equation

HRID 2275510 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[C:17]([CH:18]=1)=[N:16][C:15]1[C:10](=[CH:11][CH:12]=[C:13]([N+:19]([O-])=O)[CH:14]=1)[C:9]=2[NH2:22])(=[O:3])[CH3:2].C(OCC)(=O)C.CO.C([O-])=O.[NH4+]>O>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[C:17]([CH:18]=1)=[N:16][C:15]1[C:10](=[CH:11][CH:12]=[C:13]([NH2:19])[CH:14]=1)[C:9]=2[NH2:22])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 2723923Ammonium formate2×HCID 87629429HCID 87629429, compound

Product 1

HCID 86634099HCID 86634099, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 50 mL rbf equipped with a nitrogen bubbler were charged 3-acetamidyl-6-nitro-9-aminoacridine (110 mg, 0.37 mmol) and ethyl acetate (1.9 mL). Methanol (950 μL) and Pd/Alumina 10% (12 mg) were added and the reaction mixture was stirred to a fine suspension. Ammonium formate (47 mg, 0.74 mmol) was added and the mixture was stirred for 20 min at room temperature. A further portion of ammonium formate (70 mg, 1.11 mmol) was then added. Stirring was maintained overnight. The suspension was filtered and washed with ethyl acetate to afford the crude product (106 mg). The solid was dissolved in water and washed with ethyl acetate. The aqueous layer was concentrated in vacuo to afford 3-acetamidyl-6,9-diaminoacridine as a brown solid (29 mg, 29%). 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 suspension was filtered
  6. washwashed with ethyl acetate
  7. customto afford the crude product (106 mg)
  8. washwashed with ethyl acetate
  9. concentrationThe aqueous layer was concentrated in vacuo

Sources & evidence

ORD record
ord-0247e0d8be5f416ea20474d27c4d4b64
Source dataset
uspto-grants-2015_09
Patent number
US09127164B2

Reaction notes

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