Bromomethylcyclopropane → 2-(Cyclopropylmethoxy)-5-nitropyridine

HRID 1898316노트

반응식

HRID 1898316 반응식
[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

참가 물질

4

반응물 2

HCID 81503BromomethylcyclopropaneHCID 178526703HCID 178526703, 화합물

생성물 1

HCID 675034292-(Cyclopropylmethoxy)-5-nitropyridine수율 28.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b7e209a2fc64496ab19196ed74405b33
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08519149B2

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