Ammonia → Imiquimod

HRID 1789438Notes

Reaction equation

HRID 1789438 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 (0.0231 mole) of 4-chloro-1-isobutyl-1H-imidazo[4,5-c]quinoline from Step (D) above and 30 ml of 20% ammonia in methanol was heated in a steel bomb for about 8 hours at about 145° C. The bomb was allowed to stand overnight at room temperature. The bomb was then cooled in an ice bath, and the solid therein was filtered, washed with methanol, and dried. Recrystallization from N,N-dimethylformamide provided 4.1 g of 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine, m.p. 288°-291° C.

Workup

  1. temperatureThe bomb was then cooled in an ice bath
  2. filtrationthe solid therein was filtered
  3. washwashed with methanol
  4. customdried
  5. customRecrystallization from N,N-dimethylformamide

Sources & evidence

ORD record
ord-9f8211210c6d4dbf81d1600cda775b83
Source dataset
uspto-grants-1987_08
Patent number
US04689338

Reaction notes

Loading…