Methane → alpha-Methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2-methanol
Reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:17](O)(=O)[CH:18]([CH3:20])[OH:19].C>Cl>[CH3:17][CH:18]([C:20]1[N:12]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1)[OH:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
3-Amino-4-(2-methylpropylamino) quinoline (29.0 g; 0.135 mol) and lactic acid (36 mL; 0.48 mol) were mixed and heated at 140° C. for 6 hr. The mixture was then dissolved in dilute hydrochloric acid and treated with charcoal. The solids were filtered from the mixture. The filtrate was made basic with ammonium hydroxide to precipitate the product as an oil. The oil was extracted into ethyl acetate. The ethyl acetate solution was treated with decolorizing carbon and the solids were filtered from the mixture. The filtrate was evaporated to dryness to yield a greenish oil which was pure enough for further reactions. A small sample was triturated with hexane to obtain a solid which was recrystallized from ethyl acetate for analysis. m.p. 152-166° C. Analysis: Calculated: C, 71.4; H, 7.11; N, 15.6. Found: C, 71.1; H, 7.33; N, 15.4.
Workup
- filtrationThe solids were filtered from the mixture
- customto precipitate the product as an oil
- extractionThe oil was extracted into ethyl acetate
- additionThe ethyl acetate solution was treated with decolorizing carbon
- filtrationthe solids were filtered from the mixture
- customThe filtrate was evaporated to dryness
- customto yield a greenish oil which
- customA small sample was triturated with hexane
- customto obtain a solid which
- customwas recrystallized from ethyl acetate for analysis
Sources & evidence
- ORD record
- ord-428cb1d11dfd488dad596dfa5769361b
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05977366
Reaction notes
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