Hydrochloric Acid → 2-Allylamino-6-methylnicotinic acid methyl ester

HRID 2058183

Reaktionsgleichung

Reaktionsgleichung von HRID 2058183
Cl[C:2]1[N:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:13]([NH2:16])[CH:14]=[CH2:15].C(=O)([O-])[O-].[Na+].[Na+].Cl>C(OCC)C.C(O)C>[CH3:7][O:6][C:4](=[O:5])[C:3]1[CH:8]=[CH:9][C:10]([CH3:12])=[N:11][C:2]=1[NH:16][CH2:13][CH:14]=[CH2:15]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7853AllylamineHCID 10340Sodium CarbonateHCID 13055804Methyl 2-chloro-6-methylpyridine-3-carboxylate

Produkt 1

HCID 128186562-Allylamino-6-methylnicotinic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherKatalysatorHCID 702EthanolLösungsmittel2×

Versuchsvorschrift

A stirred mixture of 9.25 g. (0.05 mole) of methyl 2-chloro-6-methylnicotinate, 2,85 g. (0.05 mole) of allylamine and 5.3 g. (0.05 mole) of sodium carbonate in 50 ml. of ethanol was heated under reflux for 5 hours. The mixture was filtered and the filtrate was evaporated in a rotary evaporator. The residue was diluted with 50 ml. of water and was extracted with 50 ml. of diethyl ether. The ether layer was dried over magnesium sulfate, filtered and was evaporated. The residue was passed through a neutral aluminum oxide column using ethyl acetate as the eluent. Evaporation of the ethyl acetate gave 3.1 g. of product. A small amount of this oil was dissolved in diethyl ether containing a few drops of ethanol and this solution was acidified with an ethereal hydrochloric acid solution. The precipitate which formed was collected and was recrystallized from ethyl acetate to give 2-allylamino-6-methylnicotinic acid methyl ester, m.p. 140°-2° C.

Aufarbeitung

  1. additionA stirred mixture of 9.25 g
  2. temperatureunder reflux for 5 hours
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated in a rotary evaporator
  5. additionThe residue was diluted with 50 ml
  6. extractionof water and was extracted with 50 ml
  7. dry with materialThe ether layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. customwas evaporated
  10. customEvaporation of the ethyl acetate
  11. customgave 3.1 g
  12. customThe precipitate which formed
  13. customwas collected
  14. customwas recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-810224417b354735ba82b7500626e8b1
Quelldatensatz
uspto-grants-1980_07
Patentnummer
US04215123

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