1,10-Phenanthroline → 3-(4-Methyl-2-oxo-2H-pyridin-1-yl)-5-nitro-benzoic acid methyl ester

HRID 84728

反応式

HRID 84728 の反応式
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[CH3:9][O:10][C:11](=[O:22])[C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[C:14](I)[CH:13]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>[Cu]I.O1CCOCC1>[CH3:9][O:10][C:11](=[O:22])[C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[C:14]([N:3]2[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]2=[O:1])[CH:13]=1

参加物

7

反応物 4

HCID 13181,10-PhenanthrolineHCID 62657Potassium Phosphate, TribasicHCID 7020599Methyl 3-iodo-5-nitrobenzoate2 回HCID 178428601HCID 178428601、化合物2 回

生成物 1

HCID 578513253-(4-Methyl-2-oxo-2H-pyridin-1-yl)-5-nitro-benzoic acid methyl ester収率 99.9%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

To a 25 ml round-bottomed flask was added 2-Hydroxy-4-methylpyridine (17.9 mg, 0.164 mmol), 3-Iodo-5-nitro-benzoic acid methyl ester (40 mg, 0.137 mmol), CuI (5.2 mg, 0.027 mmol) and 1,4-dioxane (10 ml). The reaction mixture was stirred for 5 minutes to the dissolve 2-Hydroxy-4-methylpyridine and 3-iodo-5-nitro-benzoic acid methyl ester, after which 1,10-phenanthroline (9.84 mg, 0.055 mmol) was added, followed by K3PO4 (174 mg, 0.082 mmol). The reaction mixture was flushed with N2, and heated to 110° C. for 24 hours. After cooling to room temperature, the mixture was diluted with H2O, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography to give 3-(4-Methyl-2-oxo-2H-pyridin-1-yl)-5-nitro-benzoic acid methyl ester (39.45 mg, 61%) as light yellow solid. MS (M+H)=289.

後処理

  1. customThe reaction mixture was flushed with N2
  2. temperatureAfter cooling to room temperature
  3. additionthe mixture was diluted with H2O
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-abc31ea669f04fa9b7f70a3f3681bc8e
出典データセット
uspto-grants-2014_09
特許番号
US08846945B2

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