Acetic Anhydride → HCID 9879755, compound

HRID 1699670Notes

Reaction equation

HRID 1699670 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-9492b11385f343daa7c2e23010967390
Source dataset
uspto-grants-2002_02
Patent number
US06348462B1

Reaction notes

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