Hydrochloric Acid → HCID 86612260, compound

HRID 1623172Notes

Reaction equation

HRID 1623172 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:21][O:22][CH2:23][CH3:24])[N:14]([CH2:15][CH2:16][CH2:17][C:18](=O)[CH3:19])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[ClH:25].[CH3:26][O:27][NH2:28].C(O)C.Cl>C(OCC)C>[ClH:25].[CH3:26][O:27][N:28]=[C:18]([CH2:17][CH2:16][CH2:15][N:14]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=[C:13]1[CH2:21][O:22][CH2:23][CH3:24])[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 521874O-Methylhydroxylamine hydrochlorideHCID 58837337HCID 58837337, compound

Product 1

HCID 86612260HCID 86612260, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

By the general method described in Part F of Example 30, 5-(4-amino-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one was reacted with O-methylhydroxylamine hydrochloride. The product was dissolved a mixture of ethanol and diethyl ether, and a solution of hydrogen chloride (1 equivalent of a 1.0 M solution in diethyl ether) was added. A precipitate formed, and the solvents were removed under reduced pressure. The resulting solid was recrystallized from a mixture of ethanol and diethyl ether to provide 5-(4-amino-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one O-methyloxime hydrochloride in about a 6.4 to 1 mixture of E and Z isomers as a white solid, mp 189-192° C.

Workup

  1. dissolutionThe product was dissolved
  2. customA precipitate formed
  3. customthe solvents were removed under reduced pressure
  4. customThe resulting solid was recrystallized from a mixture of ethanol and diethyl ether

Sources & evidence

ORD record
ord-771eb192dbd049edb0b311cbaf09b18b
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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