Dimethyl Sulfoxide → HCID 86052444, compound

HRID 521268Notes

Reaction equation

HRID 521268 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21])=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2].CS(C)=O.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C>>[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[O:21])=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22320550HCID 22320550, compound

Product 1

HCID 86052444HCID 86052444, compoundYield 99.6%

Procedure

The alcohol from Step 1, 6-(3-nitro-quinolin-4-ylamino)hexan-1-ol (10.0 g, 34.6 mmol), was oxidized by the general method described in Step 6 of Example 1 with DMSO (4.05 g, 51.8 mmol), oxalyl chloride (4.83 g, 38.0 mmol), and triethylamine (10.5 g, 104 mmol) to provide 6-(3-nitroquinolin-4-ylamino)hexanal (9.9 g) as a bright yellow solid that was used directly in the next step without further purification.

Sources & evidence

ORD record
ord-4b0195862c0c4783a947a32915e4e050
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

Loading…