Hydrochloric Acid → HCID 21470207, compound

HRID 1938802Notes

Reaction equation

HRID 1938802 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][CH2:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]([CH3:19])([CH3:18])[OH:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.Cl.C(OCC)C>FC(F)(F)C(O)=O.CO.[Pt](=O)=O>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][CH2:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]([CH3:18])([CH3:19])[OH:17])[C:10]=2[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 21470208HCID 21470208, compound

Product 1

HCID 21470207HCID 21470207, compoundYield 69.1%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 887MethanolSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Platinum (IV) oxide (0.3 g) was added to a suspension of 4-amino-2-butyl-α,α,-dimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol (1.0 g, 3.2 mmole) in trifluoroacetic acid (20 mL). The mixture was hydrogenated at 50 psi (3.44×105Pa) for 3 days. The reaction mixture was filtered to remove the catalyst then concentrated under vacuum. The resulting residue was covered with water and aqueous sodium bicarbonate. A white solid was isolated by filtration then recrystallized for ethyl acetate. The reaction was repeated using 1.5 g of starting material. The combined products were taken up in dichloromethane, washed with 10% sodium hydroxide, dried over magnesium sulfate, then concentrated under vacuum. The material was recrystallized from ethyl acetate then from toluene to provide 1.15 g of crude product. This material was dissolved in methanol then combined first with one equivalent of hydrochloride acid then with diethyl ether. The resulting salt was converted back to the free base then purified by silica gel column chromatography diluting with 10% methanol in ethyl acetate. The resulting material was recrystallized from toluene then dried under vacuum at 110° C. to provide 0.7 g of 4-amino-2-butyl-α,α,-dimethyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinoline-1-ethanol as a solid, m.p. 160°-161.5° C. Analysis: Calculated for C18H28N4O: % C, 68.32; % H, 8.92; % N, 17.70; % C, 67.96; % H, 89.95; % N, 17.48.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationthen concentrated under vacuum
  4. customA white solid was isolated by filtration
  5. customthen recrystallized for ethyl acetate
  6. washwashed with 10% sodium hydroxide
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under vacuum
  9. customThe material was recrystallized from ethyl acetate
  10. customfrom toluene to provide 1.15 g of crude product
  11. customthen purified by silica gel column chromatography
  12. additiondiluting with 10% methanol in ethyl acetate
  13. customThe resulting material was recrystallized from toluene
  14. customthen dried under vacuum at 110° C.

Sources & evidence

ORD record
ord-a5e1ea3aadec4319b705fa44e5274f16
Source dataset
uspto-grants-1997_12
Patent number
US05693811

Reaction notes

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