Acetone → HCID 67771606, compound

HRID 374974Notes

Reaction equation

[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].C1(CN(CC2C=CC=CC=2)[C:17]2[C:26]3[N:27]=[C:28]([CH2:30][CH2:31][CH2:32][CH2:33]Cl)[NH:29][C:25]=3[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=2)C=CC=CC=1.[CH3:42][C:43]([CH3:45])=O>>[C:43]1([CH2:45][N:29]([CH2:25][C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[C:24]3[C:19]=2[N:18]=[CH:17][C:26]2[N:27]=[C:28]4[CH2:30][CH2:31][CH2:32][CH2:33][N:29]4[C:25]3=2)[CH:32]=[CH:31][CH:30]=[CH:28][CH:42]=1

Participants

Reactant 4

HCID 180Acetone

HCID 5238Sodium Iodide

HCID 11430Potassium Carbonate

HCID 178478462HCID 178478462, compound

Product 1

HCID 67771606HCID 67771606, compound

Procedure

Sodium iodide (1 g, 6 mmole) and potassium carbonate (0.8 g, 6 mmole) were added to a solution of N,N-bis(phenylmethyl)-2-(4-chlorobutyl)-1H-imidazo[4,5-c]quinolin-4-amine (0.55 g, 1.2 mmole) in acetone. The reaction mixture was heated at reflux for 4 hours, filtered, and then concentrated under vacuum. The residue was purified by flash chromatography (silica gel eluting with 10-15% ethyl acetate in hexanes v/v). Nuclear magnetic resonance spectroscopy indicated the possible presence of iodo intermediate; so the residue was taken up in acetone, combined with sodium iodide and potassium carbonate and heated at reflux over night. The reaction was worked up to provide 0.38 g of N,N-bis(phenylmethyl)-8,9,10,11 tetrahydropyrido-[1',2':1,2]imidazo[4,5-c]quinolin-4-amine.

Workup

temperatureThe reaction mixture was heated
temperatureat reflux for 4 hours
filtrationfiltered
concentrationconcentrated under vacuum
customThe residue was purified by flash chromatography (silica gel eluting with 10-15% ethyl acetate in hexanes v/v)
temperatureheated
temperatureat reflux over night

Sources & evidence

ORD record: ord-17b0f1e9ddb74d6a83500e3df8ccc271
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05482936

Reaction notes

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