Calcium Carbonate → 4-Amino-2,6-dimethyl-3-iodopyridine

HRID 2254886

Reaktionsgleichung

Reaktionsgleichung von HRID 2254886
I(Cl)(=O)=O.[I:5](Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1.[NH2:20][C:21]1[CH:26]=[C:25]([CH3:27])[N:24]=[C:23]([CH3:28])[CH:22]=1.C(=O)([O-])[O-].[Ca+2]>ClCCl.CO>[NH2:20][C:21]1[CH:26]=[C:25]([CH3:27])[N:24]=[C:23]([CH3:28])[C:22]=1[I:5]

Komponenten

5

Edukt 3

HCID 10112Calcium CarbonateHCID 770474-Amino-2,6-dimethylpyridineHCID 56924451Trimethylbenzylammonium Dichloroiodate

Produkt 1

HCID 129999544-Amino-2,6-dimethyl-3-iodopyridineAusbeute 61,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

Benzyltrimethylammonium dichloroiodate (6 g) was added to 4-amino-2,6-dimethylpyridine (2.1 g) and calcium carbonate (2.25 g) in dichloromethane/methanol (55 ml) (8:3 v/v) and the mixture was stirred for 16 hours. Solvent was removed by evaporation and the residue partitioned between 5% sodium metabisulphite solution and dichloromethane. The aqueous phase was separated and washed with dichloromethane. The aqueous phase was then basified with sodium carbonate and extracted with dichloromethane. The organic phase was washed with water, saturated sodium chloride solution and dried (MgSO4). Solvent was removed by evaporation and the residue purified by flash chromatography eluting with dichloromethane/methanol (9:1 v/v) to give 4-amino-2,6-dimethyl-3-iodopyridine (B) (1.7 g) as a light yellow solid, m.p. 103°-110° C.; NMR (CDCl3): 2.3(s,3H), 2.7(s,3H), 4.6(br s,2H), 6.3(s,1H); mass spectrum (chemical ionisation): 249 (M+H)+.

Aufarbeitung

  1. customSolvent was removed by evaporation
  2. customthe residue partitioned between 5% sodium metabisulphite solution and dichloromethane
  3. customThe aqueous phase was separated
  4. washwashed with dichloromethane
  5. extractionextracted with dichloromethane
  6. washThe organic phase was washed with water, saturated sodium chloride solution
  7. dry with materialdried (MgSO4)
  8. customSolvent was removed by evaporation
  9. customthe residue purified by flash chromatography
  10. washeluting with dichloromethane/methanol (9:1 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-8999635297044fc28e53e277a1217eb5
Quelldatensatz
uspto-grants-1993_08
Patentnummer
US05236937

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