Phosphorus pentachloride → 6-Chloro-2-methyl-3-nitropyridine
Reaction equation
[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]=1Participants
7
Reactant 5
HCID 24819Phosphorus pentachloride
HCID 12682302-Chloro-6-methyl-3-nitropyridine
HCID 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-benzodiazepine
HCID 178426723HCID 178426723, compound
HCID 1784796677-Bromo-2,3,4,5-tetrahydro-1-(1H-imidazol-4-ylmethyl)-4-(1-naphthalenylcarbonyl)-1H-1,4-benzodiazepine, hydrochlorideProduct 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 92 °C
Procedure
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.
Workup
- temperaturecooled to 0° C
- additionIce was added
- custompartitioned
- washThe aqueous layer was washed with toluene
- dry with materialthe combined organic phases were dried (magnesium sulfate)
- filtrationfiltered
- customevaporated
- customto afford
Sources & evidence
- ORD record
- ord-4e129fb7444641a7905a612e737b6e32
- Source dataset
- uspto-grants-2000_01
- Patent number
- US06011029
Reaction notes
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