Diazomethane → HCID 178497913, Verbindung

HRID 487064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 487064
[N+](=[CH2:3])=[N-].[OH:4][C:5]1[N:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]>CCOCC.C1COCC1>[OH:4][C:5]1[N:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:6]=1[C:7]([O:9][CH3:3])=[O:8]

Komponenten

5

Edukt 2

HCID 9550DiazomethaneHCID 178425908HCID 178425908, Verbindung

Produkt 1

HCID 178497913HCID 178497913, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Excess diazomethane in ether was added portionwise over 15 mins to 9.58 g (~60 mmoles) of 2-hydroxy-6-methyl nicotinic acid in 900 mL of THF at 0°. After stirring 2 hours, excess diazomethane was removed in vacuo. The resulting white solid was filtered and washed with hexane and dried. This fluffy solid was the required methyl ester. The filtrate was concentrated. The resulting solid was redissolved in a minimum amount of THF and hexane was added until no further precipitation was observed. Solid was filtered and washed with hexane and dried to provide more of the desired compound.

Aufarbeitung

  1. customexcess diazomethane was removed in vacuo
  2. filtrationThe resulting white solid was filtered
  3. washwashed with hexane
  4. customdried
  5. concentrationThe filtrate was concentrated
  6. dissolutionThe resulting solid was redissolved in a minimum amount of THF and hexane
  7. additionwas added until no further precipitation
  8. filtrationSolid was filtered
  9. washwashed with hexane
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-081eee156929442594546633c0e75235
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05294610

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