Glycolic Acid → 1-(2-Methylpropyl)-1H-imidazo[4,5-c]quinoline-2-methanol

HRID 396949Notes

Reaction equation

HRID 396949 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O.[C:19](OCC)(=[O:21])[CH3:20].S([O-])([O-])(=O)=O.[Mg+2].C(O)(=O)CO>Cl.[Pt]>[CH3:17][CH:16]([CH3:18])[CH2:15][N:14]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:1]=[C:20]1[CH2:19][OH:21]

Participants

7

Reactant 4

HCID 757Glycolic AcidHCID 8857Ethyl AcetateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 109993104-Isobutylamino-3-nitroquinoline

Product 1

HCID 152244061-(2-Methylpropyl)-1H-imidazo[4,5-c]quinoline-2-methanolYield 89.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
155 °C

Procedure

3-Nitro-4-(2-methylpropylamino)quinoline (36.8 g; 0.15 mol) was added to a mixture of ethyl acetate (300 mL), 5% Pt/C (about 1 g), and magnesium sulfate (30 g). The mixture was hydrogenated at about 50 psi initial pressure. When hydrogenation was complete the solids were filtered from the mixture and the ethyl acetate was evaporated. The resulting intermediate diamine was mixed with glycolic acid (26.9 g; 0.35 mol) and the mixture was heated at 150-160° C. for about 3 hr with occasional manual stirring. The reaction mixture was then dissolved in dilute hydrochloric acid and treated with decolorizing carbon, and the solids were filtered from the mixture. The filtrate was made basic with ammonium hydroxide to precipitate the product as a greenish solid. The solid was filtered and dried to give 34.3 g (89.6%) of crude product. The solid was reprecipitated a second time as above and the product recrystallized from ethyl acetate to give greenish crystals, m.p. 165-168° C. Analysis: Calculated: C, 70.6; H, 6.7; N, 16.5. Found: C, 70.4, H, 6.7; N, 16.3.

Workup

  1. filtrationwere filtered from the mixture
  2. customthe ethyl acetate was evaporated
  3. additiontreated with decolorizing carbon
  4. filtrationthe solids were filtered from the mixture
  5. customto precipitate the product as a greenish solid
  6. filtrationThe solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-8951d7fa6fbb40d285dd551a5251ff58
Source dataset
uspto-grants-2003_08
Patent number
US06608201B2

Reaction notes

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