Ammonium Hydroxide → Imiquimod

HRID 1789416Notes

Reaction equation

HRID 1789416 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.[OH-].[NH4+:20]>>[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]([NH2:20])[C:11]=2[N:12]=[CH:13]1)[CH:16]([CH3:18])[CH3:17]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 3839614-chloro-1-isobutyl-1H-imidazo[4,5-c]quinoline

Product 1

HCID 57469Imiquimod

Conditions

Temperature
150 °C

Procedure

A mixture of 4.0 g (0.0154 mole) of 4-chloro-1-isobutyl-1H-imidazo [4,5-c]quinoline (from Example 77) and 25 cc of concentrated ammonium hydroxide was placed in a metal bomb and heated at 150° C. for about 16 hours. After cooling the solid was separated by filtration, washed with water and recrystallized from ethanol to provide white crystals of 1-isobutyl-1H-imidazo [4,5-c]quinolin-4-amine, m.p. 288°-291° C. Recrystallization from N,N-dimethylformamide is preferred. Analysis: Calculated for C14H16N4 : % C, 70.0; H, 6.7; % H, 23.3; Found: % C, 69.3; % H, 6.6; % N, 23.2.

Workup

  1. temperatureAfter cooling the solid
  2. customwas separated by filtration
  3. washwashed with water
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-dbffeec5148f4326a5a271f967528eb5
Source dataset
uspto-grants-1987_08
Patent number
US04689338

Reaction notes

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