Ethanol → Imiquimod

HRID 2246821Notes

Reaction equation

HRID 2246821 reaction equation
C([NH:8][C:9]1[C:18]2[N:19]=[CH:20][N:21]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1)C1C=CC=CC=1.C(O)C.[H][H]>[OH-].[OH-].[Pd+2].C(N(CC)CC)C>[NH2:8][C:9]1[C:18]2[N:19]=[CH:20][N:21]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 156063074-(N-benzylamino)-1-isobutyl-1H-imidazo(4,5-c)quinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 57469Imiquimod

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8471TriethylamineSolvent

Procedure

1.0 gram of 4-(N-benzylamino)-1-isobutyl-1H-imidazo(4,5-c)quinoline is added to 10 mL of ethanol, followed by the addition of 0.03 gram triethylamine and 0.2 gram of Pearlman's catalyst (20% Pd(OH)2/C). The mixture is stirred at 40° C. under 1 atm hydrogen until completion. The mixture is then filtered through Celite® and the filtrate, containing 4-amino-1-isobutyl-1H-imidazo(4,5-c)quinoline (imiquimod), is concentrated in vacuo.

Workup

  1. filtrationThe mixture is then filtered through Celite®
  2. additionthe filtrate, containing 4-amino-1-isobutyl-1H-imidazo(4,5-c)quinoline (imiquimod)
  3. concentrationis concentrated in vacuo

Sources & evidence

ORD record
ord-c5301d2b253240f485c96a227de3897c
Source dataset
uspto-grants-2010_03
Patent number
US07687628B2

Reaction notes

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