Oxalic acid dihydrate → 6-Chloro-1-methylquinoxaline-2,3(1H,4H)-dione

HRID 1494338노트

반응식

HRID 1494338 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH3:9])=[C:4]([N+:10]([O-])=O)[CH:3]=1.O.O.[C:15]([OH:20])(=O)[C:16](O)=[O:17]>C(O)C.Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[N:8]([CH3:9])[C:16](=[O:17])[C:15](=[O:20])[NH:10]2

참가 물질

5

반응물 2

HCID 61373Oxalic acid dihydrateHCID 27368364-chloro-N-methyl-2-nitroaniline

생성물 1

HCID 32931736-Chloro-1-methylquinoxaline-2,3(1H,4H)-dione수율 23%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 702Ethanol용매

실험 절차

A suspension of 4-chloro-1-methylamino-2-nitrobenzene (1.73 g, 9.3 mmol) in 50 ml of ethanol was hydrogenated at room temperature and 2 atm. pressure in the presence of 5% palladium-on-carbon (0.5 g) until the theoretical amount of hydrogen was absorbed. The catalyst was filtered off, and 50 ml of 1N hydrochloric acid was added to the filtrate. The acidic filtrate was evaporated to dryness and the solid residue was refluxed with oxalic acid dihydrate (1.4 g, 11 mmol) in 100 ml of 4M hydrochloric acid for 90 min. The mixture was cooled and the precipitated product was collected by filtration and washed with water, ethanol and ether to give 0.45 g (23%) of the title compound. M.p. 341.5° C. (N,N-dimethylformamide): IR (KBr): 1700, 1660 cm-1, 1H-NMR (DMSO-d6 : 3.43 (s, 3H, CH3), 6.97-7.40 (m, 3H, ArH), 12.0 (broad s, 1H, NH); MS m/z: 212 (M+ +2, 50%), 210 (M+, 100%).

후처리

  1. customwas hydrogenated at room temperature
  2. custom2 atm. pressure in the presence of 5% palladium-on-carbon (0.5 g) until the theoretical amount of hydrogen was absorbed
  3. filtrationThe catalyst was filtered off
  4. addition50 ml of 1N hydrochloric acid was added to the filtrate
  5. customThe acidic filtrate was evaporated to dryness
  6. temperatureThe mixture was cooled
  7. filtrationthe precipitated product was collected by filtration
  8. washwashed with water, ethanol and ether

출처 및 근거

ORD 기록
ord-dc57de53cbba4d838f9f03fce33e1566
출처 데이터셋
uspto-grants-1991_06
특허 번호
US05026704

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