Ammonia → Imiquimod

HRID 1450694Notes

Reaction equation

HRID 1450694 reaction equation
Cl[C:2]1[C:11]2[N:12]=[CH:13][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.[NH3:19]>CO>[CH3:17][CH:16]([CH3:18])[CH2:15][N:14]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:19])[C:11]=2[N:12]=[CH:13]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 3839614-chloro-1-isobutyl-1H-imidazo[4,5-c]quinoline

Product 1

HCID 57469ImiquimodYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (66 g), methanol (266 mL) and ammonia (46.2 g) was placed in a steel bomb and heated at 150° C. for 8 h. The resulting mixture was filtered, and the solid was washed with water and dried to afford the product 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine in 70% yield.

Workup

  1. filtrationThe resulting mixture was filtered
  2. washthe solid was washed with water
  3. customdried

Sources & evidence

ORD record
ord-5b2c25c872e34757a3824fd39195a1ee
Source dataset
uspto-grants-1997_02
Patent number
US05602256

Reaction notes

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