Potassium Carbonate → 7-Chloro-3-methyl-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester

HRID 1261781Notes

Reaction equation

HRID 1261781 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]([N:6]([C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:20](=[O:23])[CH2:21][CH3:22])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:1][O:2][C:3]([C:4]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13]2[C:14]([C:20](=[O:23])[C:21]=1[CH3:22])=[CH:15][CH:16]=[C:17]([Cl:19])[CH:18]=2)=[O:24]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 70816656Methyl (n-(5-chloro-2-propionylphenyl)-N-phenylcarbamoyl)formate

Product 1

HCID 708166537-Chloro-3-methyl-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl esterYield 73.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A stirred suspension of N-(5-chloro-2-propionyl-phenyl)-N-phenyl-oxalamic acid methyl ester (15.0 g, 43.5 mmol) in methanol (200 mL) was treated with potassium carbonate (35.0 g, 253 mmol) at 25° C. The mixture was then heated at 80° C. for 1 h. At this time, the reaction was cooled to 25° C. The resulting solids were collected by filtration through a sintered glass funnel and then washed with methanol (2×50 mL). The filtrate was concentrated in vacuo. The resulting residue was dissolved in ethyl acetate (500 mL) and was washed with water (2×200 mL). The organics were dried over sodium sulfate, filtered and concentrated in vacuo. The resulting solids were triturated with hexanes and diethyl ether to afford 7-chloro-3-methyl-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (10.5 g, 73.4%). 1H NMR (DMSO-d6) δ ppm 8.24 (d, J=8.7 Hz, 1H), 7.28-7.78 (m, 6H), 6.69 (d, J=1.7 Hz, 1H), 3.49 (s, 3H), 1.97 (s, 3H); MS m/e calcd for C18H14ClNO3 [(M+H)+] 328.0. Found 327.9.

Workup

  1. temperatureAt this time, the reaction was cooled to 25° C
  2. filtrationThe resulting solids were collected by filtration through a sintered glass funnel
  3. washwashed with methanol (2×50 mL)
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutionThe resulting residue was dissolved in ethyl acetate (500 mL)
  6. washwas washed with water (2×200 mL)
  7. dry with materialThe organics were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe resulting solids were triturated with hexanes and diethyl ether

Sources & evidence

ORD record
ord-c96bfd5657de400d9773daf639a9c546
Source dataset
uspto-grants-2013_06
Patent number
US08471027B2

Reaction notes

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