Ammonia → HCID 57550538, compound

HRID 1097573Notes

Reaction equation

HRID 1097573 reaction equation
Cl[C:2]1[C:11]2[N:12]=[C:13]([NH:16][CH3:17])[N:14]([CH3:15])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:18]>CO>[CH3:17][NH:16][C:13]1[N:14]([CH3:15])[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:18])[C:11]=2[N:12]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86227601HCID 86227601, compound

Product 1

HCID 57550538HCID 57550538, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
145 °C

Procedure

4-Chloro-N,1-dimethyl-1H-imidazo[4,5-c]quinolin-2-amine (0.280 g, 0.88 mmol) and ammonia (15 mL of a 7 N solution in methanol) were added to a high-pressure vessel, which was sealed and heated in an oven at 145° C. for two days. An analysis by LC/MS indicated the presence of starting material, and heating at 145° C. was continued for a total of two weeks. The solvent was removed under reduced pressure, and the residue was purified by automated flash chromagraphy (silica cartridge, eluting with 1-20% methanol in dichloromethane with 1% aqueous ammonium hydroxide added) to provide 153 mg of N2,1-dimethyl-1H-imidazo[4,5-c]quinoline-2,4-diamine.

Workup

  1. customwhich was sealed
  2. temperatureheating at 145° C.
  3. customwas continued for a total of two weeks
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by automated flash chromagraphy (silica cartridge, eluting with 1-20% methanol in dichloromethane with 1% aqueous ammonium hydroxide added)

Sources & evidence

ORD record
ord-2aabb4abe3434c1da2073fa02a730ddc
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

Loading…