Dichloromethane → 8-Fluoro-2-methoxyquinoline-4-carboxylic Acid Methyl Ester

HRID 47431Notes

Reaction equation

HRID 47431 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](Cl)[CH:8]=[C:7]2[C:13]([OH:15])=[O:14].C(Cl)(=O)[C:17](Cl)=[O:18].Cl[CH2:23]Cl>CN(C)C=O>[CH3:23][O:15][C:13]([C:7]1[C:6]2[C:11](=[C:2]([F:1])[CH:3]=[CH:4][CH:5]=2)[N:10]=[C:9]([O:18][CH3:17])[CH:8]=1)=[O:14]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 227451272-Chloro-8-fluoro-4-quinolinecarboxylic acid

Product 1

HCID 544876468-Fluoro-2-methoxyquinoline-4-carboxylic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

8-Fluoro-2-chloroquinoline-4-carboxylic acid (0.986 g) suspended in dichloromethane (50 ml) was treated with dimethylformamide (3 drops) and oxalyl chloride (0.76 ml) and the mixture stirred for 2 h. Solvent was removed at reduced pressure. The residue was dissolved in methanol (50 ml) containing sodium methoxide (0.54 g) and stirred for 16 h. The solvent was removed at reduced pressure and the residue triturated with water. The precipitate was collected by filtration and column chromatographed (silica gel, 10→50% ethyl acetate/hexane) to give the title compound (0.184 g) as a colourless solid. m/z (API+): 236 (MH+). 1H NMR (CDCl3) δ: 4.02 (3H, s), 4.14 (3H, s), 7.36-7.41 (2H, m), 7.49 (1H, s), 8.37 -8.41 (1H, m).

Workup

  1. customSolvent was removed at reduced pressure
  2. dissolutionThe residue was dissolved in methanol (50 ml)
  3. additioncontaining sodium methoxide (0.54 g)
  4. stirringstirred for 16 h
  5. customThe solvent was removed at reduced pressure
  6. customthe residue triturated with water
  7. filtrationThe precipitate was collected by filtration and column
  8. customchromatographed (silica gel, 10→50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-76a8eaad76fd49b48c8dcb151e9494ca
Source dataset
uspto-grants-2004_03
Patent number
US06699879B1

Reaction notes

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