Phosphorus pentachloride → 6-Chloro-2-methyl-3-nitropyridine

HRID 849404Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 849404
[C:1](C1C=CC2N(CC3N=CN(C(OC(C)(C)C)=O)C=3)C[C@@H](CC3C=CC=CC=3)N(S(C)(=O)=O)CC=2C=1)#N.O[C:39]1[C:44]([N+:45]([O-:47])=[O:46])=[CH:43][CH:42]=[C:41](C)[N:40]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[ClH:55].BrC1C=CC2N(CC3N=CNC=3)CCN(C(C3C4C(=CC=CC=4)C=CC=3)=O)CC=2C=1.ClC1C([N+]([O-])=O)=CC=C(C)N=1>C1(C)C=CC=CC=1>[Cl:55][C:41]1[CH:42]=[CH:43][C:44]([N+:45]([O-:47])=[O:46])=[C:39]([CH3:1])[N:40]=1

Komponenten

7

Edukt 5

HCID 24819Phosphorus pentachlorideHCID 12682302-Chloro-6-methyl-3-nitropyridineHCID 69841490(R)-7-cyano-2,3,4,5-tetrahydro-1-[(((1,1-dimethylethoxy)-carbonyl)-1H-imidazol-4-yl)methyl]-4-(methylsulfonyl)-3-(phenylmethyl)-1H-1,4-benzodiazepineHCID 178426723HCID 178426723, VerbindungHCID 1784796677-Bromo-2,3,4,5-tetrahydro-1-(1H-imidazol-4-ylmethyl)-4-(1-naphthalenylcarbonyl)-1H-1,4-benzodiazepine, hydrochloride

Produkt 1

HCID 2531236-Chloro-2-methyl-3-nitropyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
92 °C

Versuchsvorschrift

A mixture of Compound A, 2-hydroxy-3-nitro-6-methylpyridine (0.93 g, 6.05 mmol) and phosphorus pentachloride (48.9 g, 235 mmol) in toluene (10 mL) was heated at 92° C. for 16 hours and cooled to 0° C. Ice was added and the mixture was stirred and partitioned. The aqueous layer was washed with toluene and the combined organic phases were dried (magnesium sulfate), filtered and evaporated to afford 1.03 g of a 6:1 mixture of Compound B and 2-chloro-3-nitro-6-methylpyridine (100%) as a reddish brown crystalline semi-solid.

Aufarbeitung

  1. temperaturecooled to 0° C
  2. additionIce was added
  3. custompartitioned
  4. washThe aqueous layer was washed with toluene
  5. dry with materialthe combined organic phases were dried (magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated
  8. customto afford

Quellen und Nachweise

ORD-Eintrag
ord-4e129fb7444641a7905a612e737b6e32
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06011029

Notizen zur Reaktion

Wird geladen…