Ammonia → HCID 57550533, compound

HRID 1097561Notes

Reaction equation

HRID 1097561 reaction equation
Br.[CH2:2]([N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[C:13](Cl)[C:12]=2[N:11]=[C:10]1[NH2:23])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH3:24]>CO>[CH2:2]([N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[C:13]([NH2:24])[C:12]=2[N:11]=[C:10]1[NH2:23])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86626282HCID 86626282, compound

Product 1

HCID 57550533HCID 57550533, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
170 °C

Procedure

Crude 1-benzyl-4-chloro-1H-imidazo[4,5-c]quinoline-2-amine hydrobromide (0.500 g) and ammonia (20 mL of a 7 N solution in methanol) were added to a high-pressure vessel, which was sealed and heated in an oven at 170° C. for six days. The resulting solution was concentrated under reduced pressure, and the residue was purified by automated flash chromatography on silica gel (eluting with 0-10% methanol in dichloromethane with 1% ammonium hydroxide added) to provide 42 mg of 1-benzyl-1H-imidazo[4,5-c]quinoline-2,4-diamine as a brown powder, mp 254-256° C.

Workup

  1. customwhich was sealed
  2. concentrationThe resulting solution was concentrated under reduced pressure
  3. customthe residue was purified by automated flash chromatography on silica gel (eluting with 0-10% methanol in dichloromethane with 1% ammonium hydroxide added)

Sources & evidence

ORD record
ord-b72bc417f9e04b46a916a2e356def8e8
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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