Ammonium Hydroxide → HCID 14700378, compound

HRID 2248089Notes

Reaction equation

HRID 2248089 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH:13]([CH3:16])[CH2:14][OH:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:17](OC(OCC)OCC)(=O)C.[OH-].[NH4+]>O>[CH3:16][CH:13]([N:12]1[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]=[CH:17]1)[CH2:14][OH:15]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 84166Methanol, 1,1-diethoxy-, 1-acetateHCID 14986942HCID 14986942, compound

Product 1

HCID 14700378HCID 14700378, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-[(3-Amino-4-quinolinyl)amino]-1-propanol (0.113 mole) as a crude reaction product obtained by the method of Example 4, was mixed with a 20 percent molar excess of diethoxymethyl acetate (22.3g, 0.136 mole) and heated for 0.75 hour. To the mixture was added 150 mL of water. The resulting mixture was made basic with concentrated ammonium hydroxide, and extracted first with ethyl acetate, then with chloroform. The extracts were combined, dried over magnesium sulfate, and evaporated, slurried in 1:1 chloroform/diethyl ether and separated by filtration to provide the solid product, beta-methyl-1H-imidazo[4,5-c]-quinoline-1-ethanol, m.p. 170°-174° C. after recrystallization from ethanol with treatment with decolorizing carbon. Analysis: Calculated for C13H13N3O: %C, 68.7; %H, 5.8; %N, 18.5; Found: %C, 68.5; %H, 5.8; %N, 18.5.

Workup

  1. customobtained by the method of Example 4
  2. temperatureheated for 0.75 hour
  3. extractionextracted first with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customseparated by filtration

Sources & evidence

ORD record
ord-7a6d09978edd4c95913defbd79947335
Source dataset
uspto-grants-1991_08
Patent number
US05037986

Reaction notes

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