Phosphoric Acid → 3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-one

HRID 455550

Reaktionsgleichung

Reaktionsgleichung von HRID 455550
OP(O)(O)=O.[Br:6][C:7]1[CH:8]=[N:9][C:10]([O:16][C:17]2[CH:22]=[CH:21][C:20]([I:23])=[CH:19][CH:18]=2)=[C:11]([CH:15]=1)[C:12]([OH:14])=O>O>[Br:6][C:7]1[CH:15]=[C:11]2[C:12](=[O:14])[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([I:23])[CH:21]=3)[O:16][C:10]2=[N:9][CH:8]=1

Komponenten

4

Edukt 2

HCID 1004Phosphoric AcidHCID 574756375-Bromo-2-(4-iodophenoxy)nicotinic acid

Produkt 1

HCID 574756483-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-oneAusbeute 85,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
117.5 °C

Versuchsvorschrift

A 5 L 3-neck flask equipped with an overhead stirrer, a thermometer and nitrogen inlet was charged with PPA (4 Kg, 1942 mL) (115% H3PO4) and heated to 115-120° C. 5-Bromo-2-(4-iodophenoxy)nicotinic acid (400 g, 952 mmol) was charged portion wise to the hot PPA. The viscous mixture was then allowed to stir overnight (16-18 h) at 115-120° C. The dark viscous mixture was cooled to 60-65° C. and poured slowly onto a mixture of ice (3000 g) and water (2000 mL) under mechanical stirring. The light brown slurry was allowed to stir overnight and filtered at RT. The wet cake was washed with water (2×1000 mL) followed by IPA (1500 mL) and hexane (2×1000 mL). The solid was dried to obtain 326.4 g of 3-Bromo-7-iodo-5H-chromeno[2,3-b]pyridine-5-one as a grey solid.

Aufarbeitung

  1. customA 5 L 3-neck flask equipped with an overhead stirrer
  2. temperatureThe dark viscous mixture was cooled to 60-65° C.
  3. stirringto stir overnight
  4. filtrationfiltered at RT
  5. washThe wet cake was washed with water (2×1000 mL)
  6. customThe solid was dried

Quellen und Nachweise

ORD-Eintrag
ord-dafad0659b4240dca6fa2ce091df8046
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497264B2

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