Water → 2-Ethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

HRID 258244Notes

Reaction equation

HRID 258244 reaction equation
[CH3:1][CH:2]([CH3:16])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[NH2:15].O.[OH-].[NH4+].[C:20](O)(=O)[CH2:21][CH3:22]>>[CH2:21]([C:22]1[N:4]([CH2:3][CH:2]([CH3:16])[CH3:1])[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:15]=1)[CH3:20]

Participants

5

Reactant 4

HCID 962WaterHCID 1032Propionic AcidHCID 14923Ammonium HydroxideHCID 11298872N4-(2-methylpropyl)quinoline-3,4-diamine

Product 1

HCID 197373162-Ethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

Conditions

Temperature
120 °C

Procedure

A 16.55 g (0.077 mol) portion of N4 -(2-methylpropyl)-3,4-quinolinediamine (U.S. Pat. No. 4,689,338 example 16) was suspended in 100 mL of propionic acid and then heated at 120° C. for about 20 hours. After cooling to room temperature, the reaction mixture was poured into 300 mL of water, made basic with concentrated ammonium hydroxide, cooled in an ice bath and then extracted with diethyl ether. The volume of the ether extract was reduced under vacuum. The resulting precipitate was collected, rinsed with ether and dried to provide 11 g of crystalline solid, m.p. 72-73.5° C. Analysis: Calculated for C16H19N3 : %C, 75.8; %H, 7.6; %N, 16.6; Found: %C, 75.6; %H, 7.7; %N, 16.5.

Workup

  1. temperatureAfter cooling to room temperature
  2. temperaturecooled in an ice bath
  3. extractionextracted with diethyl ether
  4. extractionThe volume of the ether extract
  5. customThe resulting precipitate was collected
  6. washrinsed with ether
  7. customdried

Sources & evidence

ORD record
ord-963baccc56854978969595fdb7c4a4da
Source dataset
uspto-grants-1993_11
Patent number
US05266575

Reaction notes

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