Acetic Anhydride → HCID 9879755, compound

HRID 2119858Notes

Reaction equation

HRID 2119858 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:19][NH2:20])[N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22]>CO>[C:21]([NH:20][CH2:19][C:13]1[N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=1)(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 15224402HCID 15224402, compound

Product 1

HCID 9879755HCID 9879755, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Amino-1-(2-methylpropyl)-1H-imidazo-[4,5-c]quinoline-2-methanamine (1.1 g; 0.004 mol, Example 14) was added to acetic anhydride (3 mL). The mixture was stirred at room temperature for 5 hrs. The solution was then diluted with methanol (50 mL) and refluxed for 1 hr. The solution was concentrated and the residue made basic with aqueous sodium bicarbonate solution. The oily residue was extracted into dichloromethane. The extracts were dried over magnesium sulfate and evaporated to dryness. The residue was recrystallized from ethyl acetate to yield pure product m.p. 214-218° C. Analysis: Calculated: C, 65.6; H, 6.8; N, 22.5. Found: C, 65.1; H, 6.6; N, 22.0.

Workup

  1. temperaturerefluxed for 1 hr
  2. concentrationThe solution was concentrated
  3. extractionThe oily residue was extracted into dichloromethane
  4. dry with materialThe extracts were dried over magnesium sulfate
  5. customevaporated to dryness
  6. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-8a9f8ad8b90e408a8aabb3b921b3149e
Source dataset
uspto-grants-2004_02
Patent number
US06686472B2

Reaction notes

Loading…