Water → Methyl 5-nitroquinoline-8-carboxylate

HRID 1725518

Reaction equation

HRID 1725518 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2)([O-:3])=[O:2].IC.[C:19](=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:19][O:15][C:14]([C:11]1[CH:12]=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[C:5]2[C:10]=1[N:9]=[CH:8][CH:7]=[CH:6]2)=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 154053315-Nitroquinoline-8-carboxylic acid

Product 1

HCID 68521805Methyl 5-nitroquinoline-8-carboxylateYield 78.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 300 mg (1.375 mmol) of 5-nitroquinoline-8-carboxilic acid (Breckenridge, J. G. Et al., Canadian J. of Research Sect. B; 1947, 25, 49) in DMF (6 mL), 546 mg (3.850 mmol) of iodomethane and 190 mg (1.375 mmol) of potassium carbonate were added. The resulting mixture was stirred at room temperature for one hour. Water (10 mL) was added and the product collected by filtration. The residue was washed with water and dried to yield the title compound (250 mg, 78.4%).

Workup

  1. filtrationthe product collected by filtration
  2. washThe residue was washed with water
  3. customdried

Sources & evidence

ORD record
ord-5ee214cf2dbe45b78e8225f89264efb3
Source dataset
uspto-grants-2009_02
Patent number
US07491722B2

Linked notes

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