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

HRID 252941Notes

Reaction equation

HRID 252941 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-20bca2f0e3f743ca995c067b5c3719e6
Source dataset
uspto-grants-2011_01
Patent number
US07872002B2

Reaction notes

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