Bromomethylcyclopropane → 2-(Cyclopropylmethoxy)-5-nitropyridine

HRID 1898316ノート

反応式

HRID 1898316 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH:11]1([CH2:14]Br)[CH2:13][CH2:12]1>CN(C=O)C>[CH:11]1([CH2:14][O:1][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH2:13][CH2:12]1

参加物

4

反応物 2

HCID 81503BromomethylcyclopropaneHCID 178526703HCID 178526703、化合物

生成物 1

HCID 675034292-(Cyclopropylmethoxy)-5-nitropyridine収率 28.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a cold solution of 2-hydroxy-5-nitro pyridine (0.500 g, 3.57 mmol) in DMF (4.0 mL) was added cyclopropyl methyl bromide (0.481 g, 3.57 mmol) at 0° C. The reaction mass was stirred at RT for 5-6 h. The reaction mass was quenched in water and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulphate and concentrated. The obtained crude was purified by column chromatography on neutral alumina eluting with 10% EtOAc: Pet.ether to afford 0.200 g of the desired product. 1HNMR (DMSO-d6): δ 0.45-0.48 (m, 2H), 0.70-0.75 (m, 2H), 1.10-1.28 (m, 1H), 3.87 (d, J=7.2 Hz, 2H), 6.57 (d, J=10.2 Hz, 1H), 8.10 (dd, J=3.0 Hz & 2.4 Hz, 1H), 8.77 (s, 1H).

後処理

  1. customThe reaction mass was quenched in water
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated
  6. customThe obtained crude
  7. customwas purified by column chromatography on neutral alumina eluting with 10% EtOAc

出典と根拠

ORDレコード
ord-b7e209a2fc64496ab19196ed74405b33
出典データセット
uspto-grants-2013_08
特許番号
US08519149B2

反応ノート

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