Dimethylformamide → Dimethyl Quinoline-2,3-dicarboxylate

HRID 980552Notes

Reaction equation

HRID 980552 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>[N:17]1[C:11]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:1]=[C:19]([C:20]([O:22][CH3:23])=[O:21])[C:18]=1[C:24]([O:26][CH3:27])=[O:25]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 2797953HCID 2797953, compound

Product 1

HCID 11010215Dimethyl Quinoline-2,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution of dimethylformamide (DMF, 0.1 mol) in ethylenedichloride (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 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 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. customThe organic phase is separated from the aqueous phase
  8. customdried
  9. customThe solvent is removed under vacuum
  10. customthe residue recrystallized from methanol

Sources & evidence

ORD record
ord-64027e5c42554ab9b00c22c60cedba8c
Source dataset
uspto-grants-1987_01
Patent number
US04638068

Reaction notes

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