2-Nitrophenylacetonitrile → Phenylglycine nitrile

HRID 1892594Notes

Reaction equation

HRID 1892594 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]#[N:12])([O-])=O>[Pd].C(O)(=O)C>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]#[N:12]

Participants

4

Reactant 1

HCID 118882-Nitrophenylacetonitrile

Product 1

HCID 76307Phenylglycine nitrileYield 55.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A suspension of (2-nitrophenyl)-acetonitrile (30 g, 185 mmol) and 10% palladium on carbon (2 g) in acetic acid (450 mL) was hydrogenated in a Parr apparatus under 30 psi pressure at ambient temperature for 2 hours. The mixture was filtered through a Celite® pad and the filtrate was concentrated in vacuo. The obtained residue was dissolved in ethyl acetate (250 mL). The resulting solution was washed with water (2×100 mL) and saturated sodium chloride (50 mL), and then dried over anhydrous sodium sulfate and concentrated in vacuo to yield product. The crude material was purified by column chromatography (100-200 mesh silica gel) using 8% ethyl acetate in petroleum ether as eluent to afford (2-aminophenyl)acetonitrile (13.5 g, 55%) as a solid, 1HNMR (CDCl3) δ ppm 7.3-7.1 (m, 2H), (m, 2H), 3.7 (br, 2H). 3.5 (s, 2H).

Workup

  1. filtrationThe mixture was filtered through a Celite® pad
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe obtained residue was dissolved in ethyl acetate (250 mL)
  4. washThe resulting solution was washed with water (2×100 mL) and saturated sodium chloride (50 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto yield product
  8. customThe crude material was purified by column chromatography (100-200 mesh silica gel)

Sources & evidence

ORD record
ord-d05f7b910b424344bf33b6b06a9e7312
Source dataset
uspto-grants-2013_08
Patent number
US08507681B2

Reaction notes

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