Ammonia → HCID 178508167, compound

HRID 388586Notes

Reaction equation

HRID 388586 reaction equation
Cl[C:2]1[C:11]2[N:12]=[C:13]([OH:22])[N:14]([CH2:15][C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:23]>CO>[NH2:23][C:2]1[C:11]2[N:12]=[C:13]([OH:22])[N:14]([CH2:15][C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 178517323HCID 178517323, compound

Product 1

HCID 178508167HCID 178508167, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
165 °C

Procedure

4-Chloro-1-(pyridin-3-ylmethyl)-1H-imidazo[4,5-c]quinolin-2-ol (2.64 g, 8.52 mmol) and ammonia (40 mL of a 7 N solution in methanol) were added to a high-pressure vessel, which was sealed and heated in an oven at 165° C. for 42 hours and allowed to cool. A solid was present and was isolated by filtration washed with diethyl ether to provide 1.2 g of 4-amino-1-(pyridin-3-ylmethyl)-1H-imidazo[4,5-c]quinolin-2-ol. A second crop of solid (550 mg) was collected from the filtrate. A portion of the first crop was washed with dichloromethane, methanol, diethyl ether, and acetonitrile to provide a sample as tan needles, mp greater than 250° C.

Workup

  1. customwhich was sealed
  2. temperatureto cool
  3. customwas isolated by filtration
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-a736e82e164a4dcb9123e499e62103b9
Source dataset
uspto-grants-2013_02
Patent number
US08377957B2

Reaction notes

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