Dichloromethane → 4,4,6-Trimethyl-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione

HRID 2049557노트

반응식

HRID 2049557 반응식
[CH3:1][C:2]1([CH3:13])[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.C(Cl)Cl.[C:17](Cl)(=[O:21])[C:18](Cl)=[O:19]>C(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:13])[CH:11]=[C:10]([CH3:12])[C:9]2[C:4]3=[C:5]([C:17](=[O:21])[C:18](=[O:19])[N:3]13)[CH:6]=[CH:7][CH:8]=2

참가 물질

5

반응물 3

HCID 6344Dichloromethane2회HCID 89812,2,4-Trimethyl-1,2-dihydroquinolineHCID 65578Oxalyl chloride

생성물 1

HCID 15532584,4,6-Trimethyl-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

A solution of 1,2-dihydro-2,2,4-trimethylquinoline (34.6 g., 0.2 mole) in 50 ml. dry methylene chloride was added slowly dropwise to oxalyl chloride (26.4 g., 0.21 mole) in 300 ml. dry methylene chloride. Addition required 45 min., and when complete the resultant solution was stirred at ambient temperature 4 hrs. and refluxed 2 hrs. The dark red solution was freed of solvent at reduced pressure and the very dark solid residue taken up in chloroform. Dilution with ligroine and chilling produced a total yield of 32.6 g. (71.8%); m.p. 170°-176° C. A sample repeatedly recrystallized from toluene-ligroine (1:4) melted at 176°-177.5° C.

후처리

  1. temperatureand refluxed 2 hrs
  2. temperatureDilution with ligroine and chilling
  3. customproduced a total yield of 32.6 g
  4. customA sample repeatedly recrystallized from toluene-ligroine (1:4) melted at 176°-177.5° C.

출처 및 근거

ORD 기록
ord-4913fe4a055b4290be33d3596626467c
출처 데이터셋
uspto-grants-1980_04
특허 번호
US04198414

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