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

HRID 849404ノート

反応式

HRID 849404 の反応式
[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

参加物

7

反応物 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、化合物HCID 1784796677-Bromo-2,3,4,5-tetrahydro-1-(1H-imidazol-4-ylmethyl)-4-(1-naphthalenylcarbonyl)-1H-1,4-benzodiazepine, hydrochloride

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
92 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4e129fb7444641a7905a612e737b6e32
出典データセット
uspto-grants-2000_01
特許番号
US06011029

反応ノート

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