8-Nitroquinoline → 3-Iodo-8-nitroquinoline

HRID 883521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 883521
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-:3])=[O:2].[I:14]N1C(=O)CCC1=O>C(O)(=O)C>[I:14][C:10]1[CH:11]=[N:12][C:13]2[C:8]([CH:9]=1)=[CH:7][CH:6]=[CH:5][C:4]=2[N+:1]([O-:3])=[O:2]

Komponenten

4

Edukt 2

HCID 118308-NitroquinolineHCID 120273N-Iodosuccinimide2×

Produkt 1

HCID 120323673-Iodo-8-nitroquinolineAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
62 °C

Versuchsvorschrift

A stirred mixture of 8-nitroquinoline (100 g, 0.57 mol) in acetic acid (500 ml) was treated with N-iodosuccinimide (155 g, 0.69 mol) portionwise over 10 minutes, and warmed to 62° C. for 6 h. A further portion of N-iodosuccinimide (25 g, 0.14 mol) was introduced and the mixture stirred for a further 16 h before cooling to ambient temperature. The solvent was removed in vacuo, keeping the temperature below 35° C. The residue was dissolved in dichloromethane (2 L) and washed successively with saturated aqueous sodium bicarbonate solution (2×1 L), 10% aqueous sodium thiosulphate solution (1 L), water (1 L), brine (100 ml), then the organic phase was dried over magnesium sulphate. The mixture was filtered and the solvent removed to give a yellow solid which was recrystallised from ethyl acetate to give the title compound (D3) (168 g, 97%) as a yellow solid;

Aufarbeitung

  1. temperaturebefore cooling to ambient temperature
  2. customThe solvent was removed in vacuo
  3. customthe temperature below 35° C
  4. dissolutionThe residue was dissolved in dichloromethane (2 L)
  5. washwashed successively with saturated aqueous sodium bicarbonate solution (2×1 L), 10% aqueous sodium thiosulphate solution (1 L), water (1 L), brine (100 ml)
  6. dry with materialthe organic phase was dried over magnesium sulphate
  7. filtrationThe mixture was filtered
  8. customthe solvent removed
  9. customto give a yellow solid which
  10. customwas recrystallised from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-aa28125119ea4a4d9e47097b8ee0e92e
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236947B2

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