[ClH:1].[NH2:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[NH:13][CH3:14])=[CH:10][C:9]([CH3:15])=[CH:8][CH:7]=2.[C:16]([OH:20])(=O)[CH2:17][OH:18].Cl.[OH-].[Na+]>>[OH2:18].[ClH:1].[CH3:14][N:13]1[C:12]2[C:11]3[CH:10]=[C:9]([CH3:15])[CH:8]=[CH:7][C:6]=3[N:5]=[CH:4][C:3]=2[N:2]=[C:17]1[CH2:16][OH:20]A mixture of 4.5 g (0.020 mole) of 3-amino-6-methyl-4-(methylamino)quinoline hydrochloride (from Example 32), 3.8 g (0.050 mole) of glycolic acid and 75 ml of 4 N hydrochloric acid was heated at its reflux temperature for two hours. The solution was cooled, and 50% aqueous sodium hydroxide was then added to make the solution slightly basic. The precipitate was separated by filtration and washed with water. The solid was redissolved in dilute hydrochloric acid and reprecipitated with ammonium hydroxide to provide 1,8-dimethyl-2-hydroxymethyl-1H-imidazo[4,5-c]quinoline hydrochloride hydrate. Analysis: Calculated for C13H13N3O.HCl.H2O: %C, 55.4; %H, 5.7; %N, 14.9; Found: %C, 55.2; %H, 5.6; %N, 15.5.
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