4-Amino-alpha,alpha-dimethyl-1H-imidazo(4,5-c)quinolin-1-ethanol → HCID 9903314, compound

HRID 1938803Notes

Reaction equation

HRID 1938803 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[CH:13][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>FC(F)(F)C(O)=O.[Pt](=O)=O>[NH2:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][C:16]([CH3:19])([CH3:18])[OH:17])[C:10]=2[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

4

Reactant 1

HCID 1307144-Amino-alpha,alpha-dimethyl-1H-imidazo(4,5-c)quinolin-1-ethanol

Product 1

HCID 9903314HCID 9903314, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

Platinum (IV) oxide (0.3g) was added to a suspension of 4-amino-α,α,-dimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol (0.5 g, 1.95 mmole, U.S. Pat. No. 4,689,338 Example 189) in trifluoroacetic acid (15 mL). The mixture was hydrogenated at 50 psi (3.44×105Pa) overnight. The reaction mixture was filtered to remove the catalyst then concentrated under vacuum. The residue was diluted with water then combined with aqueous sodium bicarbonate. The resulting precipitate was isolated by filtration. The nuclear magnetic resonance spectroscopy indicated the reduced product.

Workup

  1. customwas hydrogenated at 50 psi (3.44×105Pa) overnight
  2. filtrationThe reaction mixture was filtered
  3. customto remove the catalyst
  4. concentrationthen concentrated under vacuum
  5. additionThe residue was diluted with water
  6. customThe resulting precipitate was isolated by filtration

Sources & evidence

ORD record
ord-30d34228ed5949d1863fd6c51d4f8fcd
Source dataset
uspto-grants-1997_12
Patent number
US05693811

Reaction notes

Loading…