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

HRID 1582874Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1582874
[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

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 313Hydrochloric AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d232576d7be043ada6b0c074c84c528c
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06740650B2

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