Water → 2,3,8,9-Tetramethoxy-dibenzo[c,h]cinnoline

HRID 1582874노트

반응식

HRID 1582874 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[CH:18]=[C:17]([O:22][CH3:23])[C:16]([O:24][CH3:25])=[CH:15]2.[N:26]([O-])=O.[Na+].O.C(Cl)(Cl)Cl>C(O)(=O)C.Cl.C(OCC)(=O)C>[CH3:23][O:22][C:17]1[C:16]([O:24][CH3:25])=[CH:15][C:14]2[C:19]([CH:18]=1)=[CH:20][CH:21]=[C:12]1[C:13]=2[N:26]=[N:1][C:2]2[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]1=2

참가 물질

8

반응물 4

HCID 962WaterHCID 6212ChloroformHCID 227164342-(6,7-Dimethoxynaphthalen-2-yl)-4,5-dimethoxyanilineHCID 23668193Sodium Nitrite

생성물 1

HCID 227164282,3,8,9-Tetramethoxy-dibenzo[c,h]cinnoline수율 44%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 313Hydrochloric Acid용매HCID 8857Ethyl Acetate용매

실험 절차

6-(2-Amino-4,5-dimethoxyphenyl)-2,3-dimethoxynaphthalene (18) (11 mg, 0.033 mmol) in acetic acid (0.6 mL) and concentrated hydrochloric acid (0.06 mL) was cooled to 0° C. and diazotised with a solution of sodium nitrite (0.026 g in 0.5 mL water). The diazonium solution was allowed to rise slowly to room temperature and left overnight. Water (30 mL) was added to the red solution with some precipitate. The resulting mixture was extracted with ethyl acetate, washed with diluted sodium hydroxide solution, then with water, dried (anhydrous Na2SO4) and rotaevaporated to give the crude product. Chromatography on silica gel using 40:60 chloroform:ethyl acetate afforded the title compound (5 mg) in 44% yield; 1H NMR (CDCl3) d 4.09(3H, s), 4.18(6H, s), 4.23(3H, s), 7.31(1H, s), 7.74(1H, s), 8.00(1H, s), 8.01(1H, d, J=8.5), 8.20(1H, d, J=8.9), 9.15(1H, s); 13C NMR d 56.5, 56.9, 99.9, 104.5, 107.9, 109.5, 116.9, 118.5, 118.9, 127.0, 128.4, 131.6, 141.8, 144.6, 151.1, 151.2, 152.0, 153.9.

후처리

  1. customto rise slowly to room temperature
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washwashed with diluted sodium hydroxide solution
  4. dry with materialwith water, dried (anhydrous Na2SO4)
  5. customto give the crude product

출처 및 근거

ORD 기록
ord-d232576d7be043ada6b0c074c84c528c
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06740650B2

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