Ammonia → Imiquimod

HRID 1789433Notes

Reaction equation

HRID 1789433 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>[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)[CH:16]([CH3:18])[CH3:17]

Participants

4

Reactant 2

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

Product 1

HCID 57469Imiquimod

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6.0 g (0.023 mole) of 4-chloro-1-isobuty-I-1H-imidazo[4,5-c]quinoline (from Example 77) and 30 ml of 20% ammonia in methanol was heated in a steel bomb for 18 hours at 150° C. The bomb was cooled, and the solid was separated by filtration, washed with methanol and recrystallized from N,N-dimethylformamide to provide 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine, m.p. 292°-294° C. Analysis: Calculated for C14H16N4 : % C, 70.0; H, 6.7; % N, 23.3; Found: % C, 69.9; % H, 6.7; % N, 23.6.

Workup

  1. temperatureThe bomb was cooled
  2. customthe solid was separated by filtration
  3. washwashed with methanol
  4. customrecrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-40c5db691dac434a8e856094f8e30b26
Source dataset
uspto-grants-1987_08
Patent number
US04689338

Reaction notes

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