p-Fluoronitrobenzene → 1,2,3,6-Tetrahydro-1-(4-nitrophenyl)-4-phenylpyridine

HRID 2104298ノート

反応式

HRID 2104298 の反応式
[C:1]1([C:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.C([O-])([O-])=O.[K+].[K+].F[C:29]1[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[N+:35]([C:32]1[CH:33]=[CH:34][C:29]([N:10]2[CH2:9][CH:8]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:12][CH2:11]2)=[CH:30][CH:31]=1)([O-:37])=[O:36]

参加物

7

反応物 5

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 825531,2,3,6-Tetrahydro-4-phenylpyridineHCID 516892Sodium Bicarbonate

生成物 1

HCID 47810351,2,3,6-Tetrahydro-1-(4-nitrophenyl)-4-phenylpyridine収率 42%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of 0.5 g (2.5 mmol) of 4-phenyl-1,2,3,6-tetrahydropyridine, 0.51 ml (2.8 mmol) of diisopropylethylamine, 0.71 g (5 mmol) of K2CO3, 0.40 g ((2.8 mmol) of 4-fluoronitrobenzene in 10 ml of DMF is heated at 100° C., for 24 hours. At the end of the reaction, the mixture is poured into 25 ml of a saturated solution of NaHCO3 and the product is extracted using 25 ml of AcOEt. After decantation, the organic solution is washed twice with 20 ml of water followed by 20 ml of brine, drying over magnesium sulphate, filtration and evaporation of the solvent under vacuum produce a yellow solid with a yield of 42%. Melting point: 185-192° C. (decomposition).

後処理

  1. customAt the end of the reaction
  2. extractionthe product is extracted
  3. washAfter decantation, the organic solution is washed twice with 20 ml of water
  4. dry with materialdrying over magnesium sulphate, filtration and evaporation of the solvent under vacuum
  5. customproduce a yellow solid with a yield of 42%

出典と根拠

ORDレコード
ord-98e0cf8450c14e52b78970e625611ce8
出典データセット
uspto-grants-2009_08
特許番号
US07576241B2

反応ノート

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