Dimethylformamide → 2(1H)-Quinoxalinone, 3,4-dihydro-

HRID 717764

반응식

HRID 717764 반응식
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].C(N([CH2:14][CH3:15])CC)C.CN(C=[O:20])C>>[NH:7]1[C:2]2[C:1](=[CH:6][CH:5]=[CH:4][CH:3]=2)[NH:8][CH2:15][C:14]1=[O:20]

참가 물질

4

반응물 3

HCID 6228DimethylformamideHCID 7243O-PhenylenediamineHCID 8471Triethylamine

생성물 1

HCID 1859492(1H)-Quinoxalinone, 3,4-dihydro-

반응 조건

온도
80 °C

실험 절차

To a solution of o-phenylenediamine (4 g, 37.03 mmol) in DMF (30 mL) was added triethylamine (10.3 mL, 74.06) followed by ethyl-2-bromo acetate (4.53 mL, 40.73 mmol). The reaction was stirred at RT for 16 h and at 80° C. for 3 h. The reaction was monitored by TLC. After completion of reaction, the DMF was removed under vacuum. Water (20 mL) was added to the reaction mixture, which was then extracted with EtOAc (300 mL). The organic layer was dried over sodium sulfate, concentrated under vacuum, and the product recrystallized with DCM/hexane in 1:1 ratio to obtain 2.2 g of desired compound.

후처리

  1. customAfter completion of reaction
  2. customthe DMF was removed under vacuum
  3. additionWater (20 mL) was added to the reaction mixture, which
  4. extractionwas then extracted with EtOAc (300 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customthe product recrystallized with DCM/hexane in 1:1 ratio

출처 및 근거

ORD 기록
ord-6021c58e75c1457b949ae4f6c2098976
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193728B2

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