Ammonia → Imiquimod

HRID 1901955Notes

Reaction equation

HRID 1901955 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 57469Imiquimod

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 4-chloro-l-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (0.86 g) in 7 g of a methanol solution containing 20% by weight of ammonia was placed in a steel bomb for 20 h at 150° C. After cooling to 20° C., the solid formed was collected by filtration and washed with methanol. The crude product 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine was recystallized from N,N-dimethylformamide.

Workup

  1. customthe solid formed
  2. filtrationwas collected by filtration
  3. washwashed with methanol

Sources & evidence

ORD record
ord-7bebddc6389346b090cd6e72c332227c
Source dataset
uspto-grants-1996_11
Patent number
US05578727

Reaction notes

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