Dimethylformamide → Dimethyl Quinoline-2,3-dicarboxylate

HRID 542270Notes

Reaction equation

HRID 542270 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 740%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution of dimethylformamide (DMF, 0.10 mol) in ethylene dichloride (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 vaccum, and the residue recrystallized from methanol to afford 18.2 g (0.74 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 vaccum
  11. customthe residue recrystallized from methanol

Sources & evidence

ORD record
ord-de5bf2a8dd014432b2c69d428e729c4d
Source dataset
uspto-grants-1987_04
Patent number
US04656283

Reaction notes

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