Ammonia methanol → HCID 22254486, compound

HRID 1611797Notes

Reaction equation

HRID 1611797 reaction equation
Cl[C:2]1[C:11]2[N:12]=[C:13]([CH3:27])[N:14]([CH2:15][CH2:16][O:17][CH2:18]/[CH:19]=[CH:20]/[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:28].CO>>[CH3:27][C:13]1[N:14]([CH2:15][CH2:16][O:17][CH2:18]/[CH:19]=[CH:20]/[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:28])[C:11]=2[N:12]=1

Participants

3

Reactant 2

HCID 21705897Ammonia methanolHCID 22254422HCID 22254422, compound

Product 1

HCID 22254486HCID 22254486, compound

Conditions

Temperature
150 °C

Procedure

4-Chloro-2-methyl-1-(2-{[(2E)-3-phenylprop-2-enyl]oxy}ethyl)-1H-imidazo[4,5-c]quinoline (2.12 g, 5.61 mmol), was combined with an ammonia/methanol solution (7%, 70 mL) in a bomb and heated to 150° C. for 16.5 hours and cooled to ambient temperature. Analysis indicated that the reaction was incomplete. The solution was concentrated under reduced pressure to ˜10 mL, diluted with ammonia/methanol (7%, 50 mL) and reacted in a bomb at 150° C. for 8.5 hours to complete the reaction. The solution was partitioned between dichloromethane and saturated aqueous sodium bicarbonate and the organic layer removed. The aqueous layer was saturated with sodium chloride and extracted with dichloromethane (3×). The organic fractions were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting brown solid was recrystalized from methanol to provide 0.963 g of 2-methyl-1-(2-{[(2E)-3-phenylprop-2-enyl]oxy}ethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, m.p. 111.8-112.5° C.

Workup

  1. temperaturecooled to ambient temperature
  2. concentrationThe solution was concentrated under reduced pressure to ˜10 mL
  3. additiondiluted with ammonia/methanol (7%, 50 mL)
  4. customreacted in a bomb at 150° C. for 8.5 hours
  5. customthe reaction
  6. customThe solution was partitioned between dichloromethane and saturated aqueous sodium bicarbonate
  7. customthe organic layer removed
  8. extractionextracted with dichloromethane (3×)
  9. dry with materialdried with anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe resulting brown solid was recrystalized from methanol

Sources & evidence

ORD record
ord-a1d63d0f876447e985589444cae71f75
Source dataset
uspto-grants-2006_01
Patent number
US06989389B2

Reaction notes

Loading…