Pyrrolidine → HCID 75480723, compound

HRID 2273084Notes

Reaction equation

HRID 2273084 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1>O>[N+:8]([C:5]1[CH:4]=[CH:3][C:2]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:7][N:6]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 8176205-Bromo-2-nitropyridine

Product 1

HCID 75480723HCID 75480723, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 600 mg (2.93 mmol) of 5-bromo-2-nitropyridine and 1.05 g (14.63 mmol) of pyrrolidine is heated in a Biotage microwave machine for 1 hour at 120° C. The reaction medium is diluted with water and then extracted with ethyl acetate. The organic phase is washed twice with water, dried over MgSO4 and then filtered. The filtrate is evaporated under reduced pressure and then chromatographed on silica gel, eluting with a heptane/ethyl acetate mixture from (100/0 v/v) up to (50/50 v/v) to give 410 mg of 2-nitro-5-pyrrolidin-1-ylpyridine.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed twice with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe filtrate is evaporated under reduced pressure
  6. customchromatographed on silica gel
  7. washeluting with a heptane/ethyl acetate mixture from (100/0 v/v) up to (50/50 v/v)

Sources & evidence

ORD record
ord-1d08bca20e5545d0b70ccbdc23196acb
Source dataset
uspto-grants-2015_09
Patent number
US09120812B2

Reaction notes

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