Hydrochloric Acid → HCID 20183601, compound

HRID 255536Notes

Reaction equation

HRID 255536 reaction equation
[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]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 757Glycolic AcidHCID 14798Sodium HydroxideHCID 13958355HCID 13958355, compound

Product 1

HCID 20183601HCID 20183601, compound

Procedure

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.

Workup

  1. temperaturewas heated at its
  2. temperaturereflux temperature for two hours
  3. temperatureThe solution was cooled
  4. customThe precipitate was separated by filtration
  5. washwashed with water
  6. dissolutionThe solid was redissolved in dilute hydrochloric acid
  7. customreprecipitated with ammonium hydroxide

Sources & evidence

ORD record
ord-46bebac8d1f444df907b4bba0fffa8ca
Source dataset
uspto-grants-1987_10
Patent number
US04698348

Reaction notes

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