Acetone → Ethyl 4-chloro-6-nitroquinoline-3-carboxylate

HRID 1907219Notes

Reaction equation

HRID 1907219 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16].C(Cl)(=O)C([Cl:23])=O.CN(C)C=O.CC(C)=O>C(Cl)(Cl)Cl>[Cl:23][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 178469582HCID 178469582, compound

Product 1

HCID 13430300Ethyl 4-chloro-6-nitroquinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 3a in chloroform were added 4 equivalents of oxalyl chloride followed by 0.1 equiv. of dimethylformamide. The solution was refluxed for 3 hours and was quenched with 5 M sodium hydroxide solution at 4° C. The chloroform layer was collected, washed with 100 mL water and brine solution, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Product was obtained by recrystallization using acetone. 1H-NMR (CDCl3) δ (ppm): 1.48 (3H, t, J=7.08 Hz), 4.55 (2H, q, J=7.08 Hz), 8.31 (1H, d, J=9.27 Hz), 8.62 (1H, m), 9.36 (2H, m). m/z 281.7 (MH+).

Workup

  1. temperatureThe solution was refluxed for 3 hours
  2. customwas quenched with 5 M sodium hydroxide solution at 4° C
  3. customThe chloroform layer was collected
  4. washwashed with 100 mL water and brine solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customProduct was obtained by recrystallization

Sources & evidence

ORD record
ord-b616a719657b4a23bb6c4977961ad200
Source dataset
uspto-grants-2013_12
Patent number
US08598159B2

Reaction notes

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