Sodium Hydroxide → HCID 10424175, compound

HRID 1373941Notes

Reaction equation

HRID 1373941 reaction equation
[CH:1]([NH:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:18])[C:8]=2[N:7]=[C:6]1[CH2:19][CH2:20][CH3:21])([CH3:3])[CH3:2].[OH-].[Na+]>FC(F)(F)C(O)=O.O.[Pt](=O)=O>[CH:1]([NH:4][N:5]1[C:17]2[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[N:10]=[C:9]([NH2:18])[C:8]=2[N:7]=[C:6]1[CH2:19][CH2:20][CH3:21])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 10423967HCID 10423967, compound

Product 1

HCID 10424175HCID 10424175, compoundYield 38.1%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N1-isopropyl-2-propyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (0.59 g, 2.1 mmol) in 15 mL of trifluoroacetic acid was treated with platinum(IV) oxide (0.55 g, 2.4 mmol) and shaken under an atmosphere of hydrogen (3.8×105 Pa). After 6 days, the reaction mixture was filtered through a pad of CELITE filter agent and rinsed with a mixture of 85:15:0.1 CHCl3:MeOH:TFA until the filtrate ran clear. The filtrate was concentrated under reduced pressure to yield a white foam. The material was suspended in water and treated with 50% NaOH solution until the pH reached 13. A white solid precipitated and was triturated in the basic mixture for 1 h. The white solid was collected by vacuum filtration. The solid was purified by chromatography (SiO2, 95:5:0.1 CHCl3:MeOH:NH4OH) to yield 0.23 g of N1-isopropyl-2-propyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinoline-1,4-diamine as a white solid.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of CELITE
  2. filtrationfilter agent
  3. washrinsed with a mixture of 85:15:0.1 CHCl3
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto yield a white foam
  6. customA white solid precipitated
  7. customwas triturated in the basic mixture for 1 h
  8. filtrationThe white solid was collected by vacuum filtration
  9. customThe solid was purified by chromatography (SiO2, 95:5:0.1 CHCl3:MeOH:NH4OH)

Sources & evidence

ORD record
ord-96418a5d926942d691007590926b4f46
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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