Water → 3-(formylamino)-6-bromo-3,4-dihydro-2(1H)quinolinone

HRID 327465Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 327465
[Br:1]Br.[CH:3]([NH:5][CH:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]1=[O:16])=[O:4].C([O-])(=O)C.[Na+].O>C(O)(=O)C>[CH:3]([NH:5][CH:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Br:1])[CH:13]=2)[NH:8][C:7]1=[O:16])=[O:4]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24408BromineHCID 517045Sodium AcetateHCID 179327143-(Formylamino)-3,4-dihydro-2(1H)quinolinone

Produkt 1

HCID 199194713-(formylamino)-6-bromo-3,4-dihydro-2(1H)quinolinoneAusbeute 66,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Bromine (16.0 g, 0.1 mol) was added to a stirred solution of 3-(formylamino)-3,4-dihydro-2(1H)quinolinone (19.0 g, 0.1 mol) and anhydrous sodium acetate (12.7 g, 0.2 mol) in acetic acid (500 mL). After 1 hour, water (1.5 L) was added and the precipitate was filtered off and air dried to give 17.8 g of 3-(formylamino)-6-bromo-3,4-dihydro-2(1H)quinolinone, mp 275°-282° C. (dec). This was dissolved in trifluoracetic acid (300 mL) and sodium nitrate (9.0 g) was added to the stirred solution. After 1 hour, water was added and the precipitate was filtered off and air dried to give 18.2 g of 3-(formylamino)-6-bromo-3,4-dihydro-8-nitro-2(1H)quinolinone, mp 232°-235° C.

Aufarbeitung

  1. filtrationthe precipitate was filtered off
  2. customair dried

Quellen und Nachweise

ORD-Eintrag
ord-f0fba8e53ac14ca7b73e982726f34fbb
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05273975

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