Dimethylformamide → Ethyl 1-ethyl-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 2099121Notes

Reaction equation

HRID 2099121 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2C(=[CH:10][CH:11]=1)NC=[C:6]([C:12]([OH:14])=[O:13])[C:5]2=[O:15].[C:16](=O)([O-])[O-].[K+].[K+].I[CH2:23][CH3:24].[CH3:25][N:26]([CH:28]=O)[CH3:27]>C(OCC)(=O)C>[CH2:23]([O:14][C:12]([C:6]1[C:5](=[O:15])[C:4]2[C:27](=[CH:10][CH:11]=[C:2]([I:1])[CH:3]=2)[N:26]([CH2:25][CH3:16])[CH:28]=1)=[O:13])[CH3:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 7196836-Iodo-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 57720090Ethyl 1-ethyl-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1,4-dihydro-6-iodo-4-oxo-quinoline-3-carboxylic acid (J. Ellis et al, Aust. J. Chem., 1973, 26, 907) (3.15 g, 10 mmol), potassium carbonate (6.9 g, 50 mmol) and iodoethane (15.6 g, 100 mmol) in dry DMF was heated at 70° C. with vigorous stirring. After 16 h the mixture was cooled and diluted with ethyl acetate. The resultant mixture was washed with water and the organic phase separated, dried and evaporated to yield the title compound as pale yellow solid, 1H NMR δ (CDCl3) 1.41 (3H, t, J=7.1 Hz), 1.54 (3H, t, J=7.3 Hz), 4.23 (2H, q, J=7.2 Hz), 4.40 (2H, q, J=7.1 Hz), 7.20 (1H, d, J=8.9 Hz), 7.95 (1H, dd, J=2.1 & 8.9 Hz), 8.48 (1H, s), 8.86 (1H, d, J=2.1 Hz).

Workup

  1. temperatureAfter 16 h the mixture was cooled
  2. washThe resultant mixture was washed with water
  3. customthe organic phase separated
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-f0912f4223c140528fab2fb1983503f1
Source dataset
uspto-grants-2009_08
Patent number
US07569550B2

Reaction notes

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