Triethylamine → 4-Methylbenzo[f]quinoxaline-2,3(1H,4H)-dione

HRID 1494337노트

반응식

HRID 1494337 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N+:12]([O-])=O)=[C:7]([NH:15][CH3:16])[CH:6]=[CH:5]2.C(N(CC)CC)C.Cl.NC1C=CC2C(=CC=CC=2)C=1N.O.O.[C:39]([OH:44])(=O)[C:40](O)=[O:41]>C(O)C.Cl.[Pd]>[CH3:16][N:15]1[C:7]2[CH:6]=[CH:5][C:4]3[CH:3]=[CH:2][CH:11]=[CH:10][C:9]=3[C:8]=2[NH:12][C:40](=[O:41])[C:39]1=[O:44]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 61373Oxalic acid dihydrateHCID 12224794Naphthalene-1,2-diamine hydrochlorideHCID 198278026-Bromo-2-methylamino-1-nitronaphthalene

생성물 1

HCID 198277974-Methylbenzo[f]quinoxaline-2,3(1H,4H)-dione수율 92%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 313Hydrochloric Acid용매HCID 702Ethanol용매

실험 절차

A suspension of 6-bromo-2-methylamino-1-nitronaphthalene (2.81 g, 10 mmol) and triethylamine (1.40 ml, 10 mmol) in 150 ml of 96% ethanol was hydrogenated at room temperature and atmospheric pressure in the presence of 5% palladium-on-carbon (500 mg) for 1 h. The solution was filtered directly into 50 ml of 4M hydrochloric acid under a nitrogen atmosphere. The acidic filtrate was evaporated to dryness and the solid diaminonaphthalene hydrochloride was refluxed with oxalic acid dihydrate (1.5 g, 11.9 mmol) in 25 ml of 4M hydrochloric acid without further purification. After reflux for 2 h the mixture was cooled, and the solid product was isolated by filtration and washed with water, ethanol and ether to give 2.07 g (92%) of the title compound. M.p. 332.7° C. (ethanol); IR (KBr): 1685 cm-1 ; 1H-NMR (DMSO-d6): 3.60 (s, 3H, CH3), 7.33-7.93 (m, 5H, ArH), 8.37-8.60 (m, 1H, ArH), 12.13 (broad s, 1H, NH); MS m/z: 226 (M+, 100%).

후처리

  1. customwas hydrogenated at room temperature
  2. filtrationThe solution was filtered directly into 50 ml of 4M hydrochloric acid under a nitrogen atmosphere
  3. customThe acidic filtrate was evaporated to dryness
  4. temperatureAfter reflux for 2 h the mixture
  5. temperaturewas cooled
  6. customthe solid product was isolated by filtration
  7. washwashed with water, ethanol and ether

출처 및 근거

ORD 기록
ord-162a0898f0834b4f9daaab29956707e0
출처 데이터셋
uspto-grants-1991_06
특허 번호
US05026704

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