Ethoxyacetic acid → 2-Ethoxymethyl-1-phenylmethyl-1H-imidazo[4,5-c]quinoline

HRID 1601694Notes

Reaction equation

HRID 1601694 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:20]([O:22][CH2:23][C:24](O)=O)[CH3:21].[OH-].[NH4+]>O>[CH2:20]([O:22][CH2:23][C:24]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[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)[CH3:21]

Participants

5

Reactant 3

HCID 12301Ethoxyacetic acidHCID 14923Ammonium HydroxideHCID 15224414HCID 15224414, compound

Product 1

HCID 152244452-Ethoxymethyl-1-phenylmethyl-1H-imidazo[4,5-c]quinolineYield 104.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

3-Amino-4-(phenylmethylamino)quinoline (4 g, 16 mmol) was combined with ethoxyacetic acid (4.5 mL, 48 mmol) and heated at 120° C. for about 3 hours. The reaction mixture was cooled to room temperature, diluted with water and then made basic with ammonium hydroxide. The resulting precipitate was collected to provide 5.3 g of the desired product as a solid. The structure was confirmed by nuclear magnetic resonance spectroscopy.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe resulting precipitate was collected

Sources & evidence

ORD record
ord-5f2236b4fff74061a0736f5f751e7fd0
Source dataset
uspto-grants-1999_11
Patent number
US05977366

Reaction notes

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