HCID 9860241, compound → HCID 10236325, compound

HRID 1938801Notes

Reaction equation

HRID 1938801 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH3:20])[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]=[C:13]([CH3:20])[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

4

Reactant 1

HCID 9860241HCID 9860241, compound

Product 1

HCID 10236325HCID 10236325, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

Platinum (IV) oxide (2.3 g) was added to a solution of 4-amino-α,α,2-trimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol (10 g, 32 mmole, U.S. Pat. No. 5,266,575 Comparative Example C1) in trifluoroacetic acid (200 mL). The mixture was hydrogenated at 50 psi (3.44×105Pa) for 5 days. The catalyst was removed by filtration. The filtrate was concentrated under vacuum. The residue was diluted with water then combined with aqueous 10% sodium hydroxide. This mixture was stirred for one hour. A precipitate was isolated by filtration and dried to provide 9.7 g of 4-amino-α,α,2-trimethyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinoline-1-ethanol as solid, m.p. 290°-292° C. Analysis: Calculated for C15H22N4O: % C, 65.67; % H, 8.08; % N, 20.42; Found % C, 65.45; % H, 7.68; % N, 20.52.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationThe filtrate was concentrated under vacuum
  3. additionThe residue was diluted with water
  4. customA precipitate was isolated by filtration
  5. customdried

Sources & evidence

ORD record
ord-5b81367592284e4a9109e45878fe8d7a
Source dataset
uspto-grants-1997_12
Patent number
US05693811

Reaction notes

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