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Hydrochloric Acid → 2-Methoxy-8,9-methylenedioxydibenzo[c,h]cinnoline

HRID 1582888
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1582888
[NH2:1][C:2]1[CH:7]=[C:6]2[O:8][CH2:9][O:10][C:5]2=[CH:4][C:3]=1[C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17]=[C:16]([O:21][CH3:22])[CH:15]=[CH:14]2.Cl.[N:24]([O-])=O.[Na+].O>C(O)(=O)C>[CH3:22][O:21][C:16]1[CH:15]=[CH:14][C:13]2[C:18]([CH:17]=1)=[CH:19][CH:20]=[C:11]1[C:12]=2[N:24]=[N:1][C:2]2[CH:7]=[C:6]3[O:8][CH2:9][O:10][C:5]3=[CH:4][C:3]1=2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 227164266-(2-Amino-4,5-methylenedioxyphenyl)-2-methoxynaphthaleneHCID 23668193Sodium Nitrite

Produkt 1

HCID 98612722-Methoxy-8,9-methylenedioxydibenzo[c,h]cinnolineAusbeute 11,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176
Acetic Acid
Lösungsmittel

Versuchsvorschrift

6-(2-Amino-4,5-methylenedioxyphenyl)-2-methoxynaphthalene 46 (170 mg, 0.58 mmol) was dissolved in acetic acid (4.5 mL) and concentrated hydrochloric acid (0.9 mL). The solution was cooled in an ice bath and diazotized by the dropwise addition of a solution of sodium nitrite (0.36 g in 3.6 mL water). The resulting diazonium solution was allowed to warm slowly to room temperature and left for 1 day. To the resulting red solution containing some precipitate was added 50 mL water and the mixture was extracted with ethyl acetate (30 mL×3). The organic layers were combined and washed with diluted sodium hydroxide solution first, then with water and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo. The crude product was purified by column chromatography on silica gel using 50:50 hexanes:ethyl acetate to give the pure 43 (20 mg) in 11% yield; mp 258-260° C.; IR (KBr) 2922, 1611, 1497, 1465, 1414, 1370, 1272, 1201 cm−1; UV (MeOH) 286, 228 nm (log ε=4.72, 4.41); 1H NMR (CDCl3) δ4.01 (3H, s), 6.23 (2H, s), 7.30 (1H, J=2.6), 7.48 (1H, dd, J1=9.1, J2=2.6), 7.75 (1H, s), 7.95 (1H, s), 8.00 (1H, d, J=9.2), 8.19 (1H, d, J=9.1), 9.62 (1H, d, J=9.2); 13C NMR δ56.01, 97.95, 102.88, 107.48, 108.31, 119.09, 119.61, 119.71, 120.57, 125.89, 126.56, 132.26, 134.59, 142.52, 145.88, 150.21, 152.14, 160.16; HRMS (EI) calcd for C18H12N2O3 m/z: 304.0848; found: 304.0843.

Aufarbeitung

  1. temperatureThe solution was cooled in an ice bath
  2. additionTo the resulting red solution containing some precipitate
  3. extractionthe mixture was extracted with ethyl acetate (30 mL×3)
  4. washwashed with diluted sodium hydroxide solution first
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customevaporated in vacuo
  7. customThe crude product was purified by column chromatography on silica gel using 50:50 hexanes

Quellen und Nachweise

ORD-Eintrag
ord-2c080440032e4077b78e9fd457e13794
Quelldatensatz
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06740650B2

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