Formic Acid → HCID 22132644, compound

HRID 1857189Notes

Reaction equation

[CH:1]([OH:3])=O.C(OC(=O)C)(=O)C.[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[N:19]=[CH:18][CH:17]=[C:16]2[O:25][C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=1.C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[N:19]=[CH:18][CH:17]=[C:16]2[O:25][C:26]1[CH:27]=[CH:28][C:29]([NH:32][CH:1]=[O:3])=[CH:30][CH:31]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Formic acid (0.13 ml) was added to acetic anhydride (0.27 ml), and the admixture was stirred at 60° C. for 2 hours. A solution of 6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (303 mg) in tetrahydrofuran (8 ml) was added to the reaction mixture, and the admixture was stirred at room temperature for 45 minutes. After the addition of aqueous sodium hydrogen carbonate, the reaction mixture was extracted 2 times with ethyl acetate, and the organic layer was then washed with brine and dried with anhydrous sodium sulfate. The solvent was removed by reduced-pressure distillation and the resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1) to obtain 327 mg of 6,7-dimethoxy-4-(4-formylaminophenoxy)quinoline.

Workup

stirringthe admixture was stirred at room temperature for 45 minutes
extractionthe reaction mixture was extracted 2 times with ethyl acetate
washthe organic layer was then washed with brine
dry with materialdried with anhydrous sodium sulfate
customThe solvent was removed by reduced-pressure distillation
customthe resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1)

Sources & evidence

ORD record: ord-5d68336e6de64e72b88c4ce382483711
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06143764

Reaction notes

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