Dimethylformamide → Dimethyl Quinoline-2,3-dicarboxylate

HRID 1905465노트

반응식

HRID 1905465 반응식
[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]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 2797953Dimethyl 2-(Phenylamino)-2-butenedioate

생성물 1

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

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6b12aeaf44b44891a22cf17d0524cdd2
출처 데이터셋
uspto-grants-1989_06
특허 번호
US04843162

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