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

HRID 849404노트

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HRID 849404 반응식
[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

참가 물질

7

반응물 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, 화합물HCID 1784796677-Bromo-2,3,4,5-tetrahydro-1-(1H-imidazol-4-ylmethyl)-4-(1-naphthalenylcarbonyl)-1H-1,4-benzodiazepine, hydrochloride

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
92 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4e129fb7444641a7905a612e737b6e32
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06011029

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