Iodoethane → Ethyl 6-methoxyquinoline-4-carboxylate

HRID 1666102Notes

Reaction equation

HRID 1666102 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[C:13]([OH:15])=[O:14].C([O-])([O-])=O.[K+].[K+].I[CH2:23][CH3:24]>CN(C=O)C>[CH2:23]([O:14][C:13]([C:6]1[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][CH:7]=1)=[O:15])[CH3:24]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 345824Quininic acid

Product 1

HCID 219907Ethyl 6-methoxyquinoline-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To a suspension of 6-methoxy-quinoline-4-carboxylic acid (prepared according to U.S. Pat. No. 5,338,851; 43.8 g, 215.6 mmol) in DMF (215 mL) were added K2CO3 (99%; 60.2 g, 431.2 mmol) and iodoethane (19.4 mL, 237.2 mmol). The mixture was heated at 55° C. overnight. The solvent was evaporated to dryness, and the residue was partitioned between EA (1.5 L) and water (600 mL). The org. layer was washed twice with brine (2×300 mL), dried over Na2SO4, filtered and concentrated to dryness to yield a purple solid (37.5 g).

Workup

  1. customprepared
  2. customThe solvent was evaporated to dryness
  3. customthe residue was partitioned between EA (1.5 L) and water (600 mL)
  4. washlayer was washed twice with brine (2×300 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2140f12d60fe4166885da228cff6fa4d
Source dataset
uspto-grants-2011_10
Patent number
US08044044B2

Reaction notes

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