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Hydrochloric Acid → 5-Chloro-3-[(2,6-difluorobenzyl)oxy]pyridine-2-amine

HRID 2275766
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2275766
[Cl:1][C:2]1[CH:3]=[C:4]([O:11][CH2:12][C:13]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=2[F:20])[C:5]([N+:8]([O-])=O)=[N:6][CH:7]=1.Cl.C([O-])(=O)C.[Na+]>C(O)C.[Fe]>[Cl:1][C:2]1[CH:3]=[C:4]([O:11][CH2:12][C:13]2[C:14]([F:20])=[CH:15][CH:16]=[CH:17][C:18]=2[F:19])[C:5]([NH2:8])=[N:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 867178765-Chloro-3-[(2,6-difluorobenzyl)oxy]-2-nitropyridine

Produkt 1

HCID 867178775-Chloro-3-[(2,6-difluorobenzyl)oxy]pyridine-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysator
HCID 702
Ethanol
Lösungsmittel

Versuchsvorschrift

59.7 g of 5-chloro-3-[(2,6-difluorobenzyl)oxy]-2-nitropyridine (Example 13A; 199 mmol, 1 equivalent) were initially charged in 600 ml of ethanol, 34.4 g of iron powder (616 mmol, 3.1 equivalents) were added and the mixture was heated to reflux. 152 ml of concentrated hydrochloric acid were slowly added dropwise and the mixture was boiled at reflux for a further 30 min. The reaction mixture was cooled and stirred into an ice/water mixture. The resulting mixture was adjusted to pH 5 using sodium acetate. The solid was filtered off, washed with water and air-dried and then dried under reduced pressure at 50° C. This gave 52.7 g (98% of theory) of the title compound.

Aufarbeitung

  1. temperaturethe mixture was heated to reflux
  2. temperatureat reflux for a further 30 min
  3. temperatureThe reaction mixture was cooled
  4. filtrationThe solid was filtered off
  5. washwashed with water
  6. customair-dried
  7. customdried under reduced pressure at 50° C

Quellen und Nachweise

ORD-Eintrag
ord-2ff538a1952441858b4eb1472e6a2c56
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09126998B2

Notizen zur Reaktion

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