alpha,alpha-dimethyl-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline-6-ethanol → HCID 9903314, compound

HRID 1938800Notes

Reaction equation

HRID 1938800 reaction equation
[CH3:1][C:2]([CH3:21])([OH:20])[CH2:3][N:4]1[C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]3N=N[N:19]=[C:8]3[C:7]=2[N:6]=[CH:5]1>FC(F)(F)C(O)=O.[Pt](=O)=O>[NH2:19][C:8]1[C:7]2[N:6]=[CH:5][N:4]([CH2:3][C:2]([CH3:21])([CH3:1])[OH:20])[C:16]=2[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[N:9]=1

Participants

4

Reactant 1

HCID 11832874alpha,alpha-dimethyl-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline-6-ethanol

Product 1

HCID 9903314HCID 9903314, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A catalytic amount of platinum (IV) oxide was added to a solution of α,α-dimethyl-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline-6-ethanol (0.40 g, 1.4 mmole, Example 1) in trifluoroacetic acid (10 mL). The mixture was hydrogenated at 50 psi (3.44×105Pa) for 48 hours. The catalyst was removed by filtration and washed with ethanol. The filtrate was concentrated under vacuum using heptane to azeotrope the trifluoroacetic acid. The resulting oil solidified on standing. The solid was dissolved in water containing enough hydrochloric acid to form a salt of the product. The aqueous solution was filtered through charcoal. The filtrate was made basic with ammonium hydroxide. The resulting precipitate was isolated by filtration and dried to provide 0.3 g of 4-amino-α,α-dimethyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinoline-1-ethanol as a white solid, m.p. 259.8°-261.3° C. Analysis: Calculated for C14H20N4O: % C, 64.59; % H,7.74; % N, 21.52; Found % C, 64.49; % H, 7.63; % N, 21.41.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with ethanol
  3. concentrationThe filtrate was concentrated under vacuum
  4. dissolutionThe solid was dissolved in water containing enough hydrochloric acid
  5. customto form a salt of the product
  6. filtrationThe aqueous solution was filtered through charcoal
  7. customThe resulting precipitate was isolated by filtration
  8. customdried

Sources & evidence

ORD record
ord-d9790c1ad16c41bc81d67aecfe3a2ded
Source dataset
uspto-grants-1997_12
Patent number
US05693811

Reaction notes

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