Acetic Anhydride → HCID 86634098, compound

HRID 2275509Notes

Reaction equation

HRID 2275509 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]([NH2:19])[CH:14]=1)[C:9]=2[NH2:20])(=[O:3])[CH3:2].[C:21](OC(=O)C)(=[O:23])[CH3:22]>C(O)(=O)C>[C:21]([NH:19][C:13]1[CH:12]=[CH:11][C:10]2[C:15]([CH:14]=1)=[N:16][C:17]1[C:8](=[CH:7][CH:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:18]=1)[C:9]=2[NH2:20])(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 86634099HCID 86634099, compound

Product 1

HCID 86634098HCID 86634098, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Acetamidyl-6,9-diaminoacridine (10 mg, 0.048 mmol) was dissolved in acetic acid (5 mL) and heated at reflux under a nitrogen atmosphere. Acetic anhydride (4.7 μL, 0.05 mmol) was added and reflux was continued for 10 min. On cooling to room temperature, the solution was concentrated to dryness and the residue was dissolved in water (10 mL) and washed with DCM (3×10 mL). The aqueous layer was lyophilised to give a brown solid.

Workup

  1. temperatureheated
  2. temperatureat reflux under a nitrogen atmosphere
  3. temperaturereflux
  4. concentrationthe solution was concentrated to dryness
  5. dissolutionthe residue was dissolved in water (10 mL)
  6. washwashed with DCM (3×10 mL)
  7. customto give a brown solid

Sources & evidence

ORD record
ord-596b64eba16040528ac0e4019f917078
Source dataset
uspto-grants-2015_09
Patent number
US09127164B2

Reaction notes

Loading…