Hydrochloric Acid → Methyl 5-amino-6-chloropyridine-3-carboxylate

HRID 50333

Reaktionsgleichung

Reaktionsgleichung von HRID 50333
[Cl:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.O.Cl>C(O)C.[Fe]>[NH2:12][C:11]1[C:2]([Cl:1])=[N:3][CH:4]=[C:5]([CH:10]=1)[C:6]([O:8][CH3:9])=[O:7]

Komponenten

6

Edukt 3

HCID 313Hydrochloric Acid2×HCID 962Water2×HCID 346961Methyl 6-chloro-5-nitronicotinate

Produkt 1

HCID 18412438Methyl 5-amino-6-chloropyridine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysator2×HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 1.08 g (5.00 mmol) of methyl 6-chloro-5-nitronicotinate (see A. H. Berrie, G. T. Newbold, and F. S. Spring in J. Chem. Soc., 2590, 1951) in 25 mL of absolute ethanol was mixed successively with 0.53 mL (29 mmol) of water, 3.2 g (57 mmol) of iron powder and 0.030 mL of concentrated hydrochloric acid and heated to boiling for one hour. Then equal quantities of water, iron powder and hydrochloric acid were added and the mixture was heated to boiling for 30 minutes. The precipitate formed on cooling was filtered off and washed with ethanol and the solvent was distilled off in vacuo. Yield: 0.75 g (81% of theory) of greenish-yellow solid, C7H7ClN2O2 (186.60); Rf value: 0.31 (silica gel; ethyl acetate/petroleum ether=1:4); YEF-Mass spectrum: M+=186 and 188 (chlorine isotopes).

Aufarbeitung

  1. temperatureheated
  2. temperaturethe mixture was heated
  3. waitto boiling for 30 minutes
  4. customThe precipitate formed
  5. temperatureon cooling
  6. filtrationwas filtered off
  7. washwashed with ethanol
  8. distillationthe solvent was distilled off in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5a3642bc30304728b7aadefe8ca48501
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710055B2

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