Benzaldehyde → HCID 69191480, compound

HRID 1373900Notes

Reaction equation

HRID 1373900 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([NH2:18])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2].[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCOCC>C(O)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH:19](=[N:18][N:6]1[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=[C:5]1[CH2:4][O:3][CH2:1][CH3:2])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 3283Diethyl EtherHCID 21075716HCID 21075716, compound

Product 1

HCID 69191480HCID 69191480, compoundYield 59.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 2-ethoxymethy-1H-imidazo[4,5-c]quinolin-1-amine (1.50 g, 6.19 mmol) in 50 mL of isopropanol was treated with benzaldehyde (0.66 mL, 6.50 mmol) and 10 mg of p-toluenesulfonic acid. The reaction mixture was heated to 120° C. for 3 d. The reaction mixture was cooled, and a precipitate started to form. The reaction mixture was treated with Et2O and then filtered to give N-benzylidene-(2-ethoxymethy-1H-imidazo[4,5-c]quinolin-1-yl)amine (1.21 g) as a gray solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customto form
  3. filtrationfiltered

Sources & evidence

ORD record
ord-c6407251baa442aa8d28a28325e66899
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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