Dimethyl Sulfoxide → HCID 86052440, compound

HRID 521264Notes

Reaction equation

[N:1]1([CH2:14][CH2:15][CH2:16][CH2:17][OH:18])[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.CS(C)=O.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C>>[N:1]1([CH2:14][CH2:15][CH2:16][CH:17]=[O:18])[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1

Participants

Reactant 4

HCID 679Dimethyl Sulfoxide

HCID 8471Triethylamine

HCID 65578Oxalyl chloride

HCID 66996598HCID 66996598, compound

Product 1

HCID 86052440HCID 86052440, compoundYield 50.4%

Procedure

The general method described in Step 6 of Example 1 was used to oxidize 4-(1H-imidazo[4,5-c]quinolin-1-yl)butan-1-ol (20.0 g, 82.9 mmol) with DMSO (48.6 g, 620 mmol), oxalyl chloride (58.0 g, 456 mmol), and triethylamine (126 g, 1.25 mol) to provide 4-(1H-imidazo[4,5-c]quinolin-1-yl)butyraldehyde (10.0 g) as a light orange oil after chromatography on silica gel (elution with 10% methanol in dichloromethane) followed by brief treatment with trifluoroacetic acid (0.10 g, 1 mmol) in a mixture of THF (50 mL) and water (20 mL).

Sources & evidence

ORD record: ord-981300ae71b2490fbbebfa9d846dd059
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328110B2

Reaction notes

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