Nicotinic Acid → 3-(Azidomethyl)pyridine

HRID 1866852Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1866852
[C:1](O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.C1(P([N:24]=[N+:25]=[N-:26])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>CN(C=O)C.O>[CH2:1]([N:24]=[N+:25]=[N-:26])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 938Nicotinic AcidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azide

Produkt 1

HCID 457912673-(Azidomethyl)pyridineAusbeute 84,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of nicotinic acid (1.23 g, 10.0 mmol) in DMF (15 mL) was added diphenylphosphoryl azide (2.60 mL, 12.0 mmol) followed by triethylamine (1.67 mL, 12.0 mmol). The mixture was stirred at room temperature for 2.5 h and diluted with water (50 mL). The mixture was extracted three times with EtOAc and the combined organic extracts were washed three times with water, dried (MgSO4) and concentrated. Flash chromatography of the residue (silica gel; hexane/EtOAc 7:3) provided I-3a as a white solid (1.13 g).

Aufarbeitung

  1. extractionThe mixture was extracted three times with EtOAc
  2. washthe combined organic extracts were washed three times with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-38018a0861d34872905b35ddd721e662
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07629467B2

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