Dimethylformamide → Dimethyl Quinoline-2,3-dicarboxylate

HRID 1905465Notes

Reaction equation

HRID 1905465 reaction equation
[CH3:1]N(C)C=O.P(Cl)(Cl)(Cl)=O.[C:11]1([NH:17][C:18]([C:24]([O:26][CH3:27])=[O:25])=[CH:19][C:20]([O:22][CH3:23])=[O:21])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)CCl>[CH3:27][O:26][C:24]([C:18]1[C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:1][C:12]2[C:11](=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:17]=1)=[O:25]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 2797953HCID 2797953, compound

Product 1

HCID 11010215Dimethyl Quinoline-2,3-dicarboxylateYield 74%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution of dimethylformamide (DMF, 0.10 mol) in ethylene chloride (EDC, 100 mL), cooled in an ice bath, is added dropwise with stirring phosphorous oxychloride (POCl3, 0.10 mol). The resulting solution is stirred for one and one-half hours at room temperature and then cooled in an ice bath. To the cooled solution is then added, in small increments, a solution of dimethyl 3-phenylaminobut-2-ene-dioate (0.10 mol) in ethylene dichloride. The resulting mixture is thereafter heated to reflux for three hours, cooled, and washed with half saturated brine. The organic phase is washed with half saturated brine. The organic phase is separated from the aqueous phase and dried. The solvent is removed under vacuum, and the residue recrystallized from methanol to afford 18.2 g (0.074 mol) of dimethyl-2,3-quinolinedicarboxylate, mp 105°-106.5° C.

Workup

  1. temperaturecooled in an ice bath
  2. additionTo the cooled solution is then added, in small increments
  3. temperatureThe resulting mixture is thereafter heated
  4. temperatureto reflux for three hours
  5. temperaturecooled
  6. washwashed with half saturated brine
  7. washThe organic phase is washed with half saturated brine
  8. customThe organic phase is separated from the aqueous phase
  9. customdried
  10. customThe solvent is removed under vacuum
  11. customthe residue recrystallized from methanol

Sources & evidence

ORD record
ord-6b12aeaf44b44891a22cf17d0524cdd2
Source dataset
uspto-grants-1989_06
Patent number
US04843162

Reaction notes

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