tert-Butyl cyano(5-nitropyridin-2-yl)acetate → 5-NITRO-2-PYRIDINEACETONITRILE

HRID 711355Notes

Reaction equation

HRID 711355 reaction equation
[C:1]([CH:3]([C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][N:12]=1)C(OC(C)(C)C)=O)#[N:2]>Cl.CCO>[N+:17]([C:14]1[CH:15]=[CH:16][C:11]([CH2:3][C:1]#[N:2])=[N:12][CH:13]=1)([O-:19])=[O:18]

Participants

3

Reactant 1

HCID 14381139tert-Butyl cyano(5-nitropyridin-2-yl)acetate

Product 1

HCID 120149655-NITRO-2-PYRIDINEACETONITRILEYield 100.4%

Reagents, catalysts & solvents 1

HCID 21887872Ethanol hydrochlorideSolvent

Conditions

Temperature
80 °C

Procedure

The crude product tert-butyl 2-cyano-2-(5-nitropyridin-2-yl)acetate (I-1b, 12 g, 47 mmol) was dissolved in 100 mL of HCl/EtOH (v/v 1:5) and stirred at 80° C. for 4 h. Then the mixture was concentrated, diluted with H2O, and extracted with EtOAc (4×40 mL). The combined extracts were concentrated, and the residue was purified by chromatography on silica gel (PE:EtOAc=3:1) to afford 2-(5-nitropyridin-2-yl)acetonitrile (I-1c) as a solid (7.7 g, 42.0% yield).

Workup

  1. concentrationThen the mixture was concentrated
  2. additiondiluted with H2O
  3. extractionextracted with EtOAc (4×40 mL)
  4. concentrationThe combined extracts were concentrated
  5. customthe residue was purified by chromatography on silica gel (PE:EtOAc=3:1)

Sources & evidence

ORD record
ord-a0437a0314ff43529cdf8a9311f0742a
Source dataset
uspto-grants-2015_11
Patent number
US09181264B2

Reaction notes

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