Ammonia → HCID 178490873, compound

HRID 388589Notes

Reaction equation

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

Participants

Conditions

Temperature: 150 °C

Procedure

4-Chloro-1-(4-methoxybenzyl)-1H-imidazo[4,5-c]quinolin-2-ol (2.0 g, 5.9 mmol) and ammonia (30 mL of a 7 N solution in methanol) were added to a high-pressure vessel, which was sealed and heated at 150° C. for two days. An analysis by LC/MS indicated the reaction was incomplete, and the vessel was sealed and heated at 165° C. for three days. The volatiles were removed under reduced pressure, and the residue was purified twice by automated flash chromatography (silica cartridge, eluting with aqueous ammonium hydroxide:methanol:dichloromethane in a gradient from 0:0:100 to 0.5:9.5:90). The resulting white solid was mixed with acetonitrile, isolated by filtration, and dried overnight under vacuum to provide 4-amino-1-(4-methoxybenzyl)-1H-imidazo[4,5-c]quinolin-2-ol as a white solid, mp greater than 260° C.

Workup

customwhich was sealed
customthe vessel was sealed
temperatureheated at 165° C. for three days
customThe volatiles were removed under reduced pressure
customthe residue was purified twice by automated flash chromatography (silica cartridge
washeluting with aqueous ammonium hydroxide
additionThe resulting white solid was mixed with acetonitrile
customisolated by filtration
customdried overnight under vacuum

Sources & evidence

ORD record: ord-b332526a0d7f48158bbd4c2097b7a981
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08377957B2

Reaction notes

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