Ammonia → HCID 57447112, compound

HRID 2366720Notes

Reaction equation

HRID 2366720 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]([O:18]CC)=O)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:24].[Cl-].[NH4+]>CO>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]([NH2:24])=[O:18])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 57447111HCID 57447111, compound

Product 1

HCID 57447112HCID 57447112, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl (4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)acetate (0.80 g), a solution of ammonia in methanol (35 mL of 7 N), and ammonium chloride (0.50 g) were heated in a sealed pressure vessel at 150° C. for 20 hours. The volatiles were removed under reduced pressure, and the solid residue was triturated with saturated aqueous sodium bicarbonate for one hour, isolated by filtration, and washed with water. The solid was recrystallized from methanol/water, and the crystals were washed sequentially with 25% aqueous sodium hydroxide (2×25 mL) and water (2×25 mL) and dried overnight in a vacuum oven at 70° C. to provide 0.120 g of 2-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)acetamide as light tan crystals, mp>300° C.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe solid residue was triturated with saturated aqueous sodium bicarbonate for one hour
  3. customisolated by filtration
  4. washwashed with water
  5. customThe solid was recrystallized from methanol/water
  6. washthe crystals were washed sequentially with 25% aqueous sodium hydroxide (2×25 mL) and water (2×25 mL)
  7. customdried overnight in a vacuum oven at 70° C.

Sources & evidence

ORD record
ord-1d70d2ecd64a401ea6cffe7846865b38
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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