Acetic Anhydride → HCID 9879755, compound

HRID 1599727Notes

Reaction equation

HRID 1599727 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-4ae9f4ddae734a0493fd2ccfc4cd0820
Source dataset
uspto-grants-1998_04
Patent number
US05741909

Reaction notes

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