Bromomethylcyclopropane → 2-(Cyclopropylmethoxy)-5-nitropyridine

HRID 1898316Notes

Reaction equation

HRID 1898316 reaction equation
[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

Participants

4

Reactant 2

HCID 81503BromomethylcyclopropaneHCID 178526703HCID 178526703, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-b7e209a2fc64496ab19196ed74405b33
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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