Acetic Anhydride → (Z)-1,1'-(4-(methoxymethylene)-3-oxo-3,4-dihydrocinnoline-1,2-diyl)diethanone

HRID 2236574노트

반응식

HRID 2236574 반응식
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][C:6](=[O:14])[N:5]1[C:15](=[O:17])[CH3:16])(=[O:3])[CH3:2].[C:18]([O:21][C:22](=O)C)(=O)C.COC(OC)OC>CN(C)C=O>[CH3:18][O:21]/[CH:22]=[C:7]1\[C:6](=[O:14])[N:5]([C:15](=[O:17])[CH3:16])[N:4]([C:1](=[O:3])[CH3:2])[C:13]2[C:8]\1=[CH:9][CH:10]=[CH:11][CH:12]=2

참가 물질

5

반응물 3

HCID 7918Acetic AnhydrideHCID 9005Trimethyl orthoformateHCID 218292321,2-diacetyl-1,4-dihydro-3(2H)cinnolinone

생성물 1

HCID 59300145(Z)-1,1'-(4-(methoxymethylene)-3-oxo-3,4-dihydrocinnoline-1,2-diyl)diethanone

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 1,2-diacetyl-1,4-dihydro-3(2H)cinnolinone (0.34 g, 1.5 mmol) in dimethylformamide (3.6 mL) is added acetic anhydride (5 mL), followed by trimethylorthoformate (0.64 mL). The mixture is heated at reflux for 12 hours. After cooling to room temperature, the mixture is purified by semi-preparative reverse-phase HPLC, employing a gradient elution from 5% acetonitrile in water with 0.1% trifluoroacetic acid to 100% acetonitrile over 60 minutes. The desired fractions were concentrated under reduced pressure to afford 0.18 g of (Z)-1,1′-(4-(methoxymethylene)-3-oxo-3,4-dihydrocinnoline-1,2-diyl)diethanone.

후처리

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 12 hours
  3. customthe mixture is purified by semi-preparative reverse-phase HPLC
  4. washa gradient elution from 5% acetonitrile in water with 0.1% trifluoroacetic acid to 100% acetonitrile over 60 minutes
  5. concentrationThe desired fractions were concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-87dadd7f3fac4fceb58d7727d56f23d1
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07713994B2

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