1,2-Dichloroethane → Quinoline

HRID 54233

반응식

HRID 54233 반응식
[CH:1]1[CH:6]=[C:5]2[CH:7]=[CH:8][C:9](C(O)=O)=[N:10][C:4]2=[CH:3][CH:2]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[N:10]1[C:4]2[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=2)[CH:7]=[CH:8][CH:9]=1

참가 물질

5

반응물 3

HCID 111,2-DichloroethaneHCID 7124Quinaldic AcidHCID 757711-Hydroxybenzotriazole

생성물 1

HCID 7047Quinoline수율 319.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
0 °C

실험 절차

A 100 ml RBF equipped with magnetic stir bar and N2 inlet was charged with 356 mg (2.06 mmol, 1 eq) 2-quinaldic acid in 10 ml dry DMF. The solution was cooled to 0° C. and 415 mg (3.07 mmol, 1.5 eq) HOBt was added followed by 415 mg EDC (2.16 mmol, 1.05 eq). The reaction was stirred 2 hours at 0° C. when 1.1 g (2.06 mmol, 1 eq) of free asparagine amine in 10 ml dry DMF was added. The reaction was stirred at 0° C. for 2 hours then room temperature overnight. The reaction was poured into sat. bicarb and extracted with 2×65 mL ethyl acetate. The combined organics were washed with 5% aq. citric acid, brine, dried and concentrated to 1.4 g crude foam. Purification by flash chromatography on silica gel (100% ethyl acetate) yielded 850 mg (61%) of quinoline adduct.

후처리

  1. customA 100 ml RBF equipped with magnetic stir bar and N2 inlet
  2. additionwas added
  3. customroom temperature overnight
  4. additionThe reaction was poured into sat. bicarb
  5. extractionextracted with 2×65 mL ethyl acetate
  6. washThe combined organics were washed with 5% aq. citric acid, brine
  7. customdried
  8. concentrationconcentrated to 1.4 g crude foam
  9. customPurification by flash chromatography on silica gel (100% ethyl acetate)

출처 및 근거

ORD 기록
ord-aa6c28ca5ebe489993550699923c7862
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622949

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