Hydrogen Bromide → 2,3-bis(4-Hydroxyphenyl)quinoxaline-6-carboxylic Acid

HRID 1267686

Reaktionsgleichung

Reaktionsgleichung von HRID 1267686
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=3)=[N:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:27]([OH:29])=[O:28])[CH:15]=3)[N:10]=2)=[CH:5][CH:4]=1.Br.[K+].[Br-]>C(O)(=O)C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)=[N:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:27]([OH:29])=[O:28])[CH:15]=3)[N:10]=2)=[CH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 260Hydrogen BromideHCID 253877Potassium BromideHCID 9803122,3-Bis(4-methoxyphenyl)quinoxaline-6-carboxylic acid

Produkt 1

HCID 9785422,3-bis(4-Hydroxyphenyl)quinoxaline-6-carboxylic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Into a 1000 mL three-necked round-bottomed flask equipped with a magnetic stirrer, nitrogen inlet, and a condenser, 2,3-bis(4-methoxyphenyl)-quinoxaline-6-carboxylic acid (34.7 g, 89.8 mmol) was dissolved in acetic acid (260 mL). Hydrobromic acid (500 mL) was then added to the clear, yellow mixture at room temperature. The reaction mixture was heated under reflux with vigorous stirring until the solution become homogeneous. After the red-brown mixture had been allowed to cool down on its own, it was poured into distilled water. The resulting light brown precipitate was collected by suction filtration and dried under the reduced pressure to give 31.9 g (99% crude yield) of yellow solid: mp 319-320° C. (dec.). Anal. Calcd. for C21H14N2O4: C, 70.38%; H, 3.94%; N, 7.82%. Found: C, 66.70%; H, 3.98%; N, 7.20%. FT-IR (KBr, cm−1): 1698, 3396. Mass spectrum (m/e): 358 (M+, 100% relative abundance). 1H-NMR (DMSO-d6, ppm) δ6.76-6.79 (d, 4H, Ar), 7.36-7.40 (dd, 4H, Ar), 8.09-8.12 (d, 1H, Ar), 8.21-8.25 (dd, 1H, Ar), 8.57 (d, 1H, Ar). 13C-NMR (DMSO-d6, δ in ppm): 114.93, 128.84, 129.21, 130.34, 131.11, 131.52, 139.32, 142.03, 153.75, 154.35, 158.44, 166.68.

Aufarbeitung

  1. customInto a 1000 mL three-necked round-bottomed flask equipped with a magnetic stirrer, nitrogen inlet, and a condenser
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux
  4. temperatureto cool down on its own
  5. additionit was poured
  6. distillationinto distilled water
  7. filtrationThe resulting light brown precipitate was collected by suction filtration
  8. customdried under the reduced pressure
  9. customto give 31.9 g (99% crude yield) of yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-5128e4de97954018ab05d0f7d1b4b764
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06552195B1

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