Dimethylformamide → Dimethyl Quinoline-2,3-dicarboxylate

HRID 542270ノート

反応式

HRID 542270 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 11010215Dimethyl Quinoline-2,3-dicarboxylate収率 740%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-de5bf2a8dd014432b2c69d428e729c4d
出典データセット
uspto-grants-1987_04
特許番号
US04656283

反応ノート

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