Sulfuric Acid → Methyl isonicotinate

HRID 638304

Reaktionsgleichung

Reaktionsgleichung von HRID 638304
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[C:15](=O)([O-])[O-].[Na+].[Na+]>CO>[C:1]([O:9][CH3:15])(=[O:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 5922Isonicotinic AcidHCID 10340Sodium Carbonate

Produkt 1

HCID 227085Methyl isonicotinateAusbeute 71,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A suspension of 100 g of isonicotinic acid (0.812 mol) in 250 ml of methanol was stirred and cooled to 10°. To this mixture was added dropwise 125 ml of sulfuric acid during 15 min. keeping the temperature below 20°. The reaction mixture was allowed to come to room temperature and then heated under reflux for 4.5 hr. After standing overnight it was poured onto 1 kg of ice and made alkaline with 235 g of sodium carbonate. The solid was filtered off, washed with water and with ether, and discarded. The filtrate was extracted with 3×300 ml of ether. The combined organic extracts were washed with water and with brine, dried over sodium sulfate, and concentrated in vacuo to leave 80 g (65%) of crude product as a pale oil.

Aufarbeitung

  1. temperaturecooled to 10°
  2. customthe temperature below 20°
  3. customto come to room temperature
  4. temperatureheated
  5. temperatureunder reflux for 4.5 hr
  6. filtrationThe solid was filtered off
  7. washwashed with water and with ether
  8. extractionThe filtrate was extracted with 3×300 ml of ether
  9. washThe combined organic extracts were washed with water and with brine
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-65b3708e0c1e499c9746b472280033f0
Quelldatensatz
uspto-grants-1985_12
Patentnummer
US04560692

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