3-(2-Nitrophenyl)acrylic acid → Hydrocarbostyril

HRID 1383391Notes

Reaction equation

HRID 1383391 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[CH:6]=[CH:7][C:8](O)=[O:9])([O-])=O>C(O)C.[Ni]>[NH:1]1[C:4]2[C:5](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:7][C:8]1=[O:9]

Participants

4

Reactant 1

HCID 928203-(2-Nitrophenyl)acrylic acid

Product 1

HCID 64796HydrocarbostyrilYield 57%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A slurry of 50.0 g (0.259 mol) of o-nitrocinnamic acid in 500 mL of ethanol was treated with 5 teaspoons of Raney Ni and hydrogenated on a Parr shaker overnight at an initial pressure of 50 psi. In the morning, the pressure was increased again to 50 psi and the reaction was continued for an additional 5 h. The reaction mixture was filtered to remove the catalyst and then washed through a bed of silica gel with a mixture of ethyl acetate and ethanol to remove traces of nickel salts. Evaporation of the filtrate gave the desired product in 57% yield. NMR (DMSO-d6) δ 2.45 (2H, t, J=7), 2.87 (2H, t, J=7), 6.87 (2H, d of d, J=7, 7), 7.12 (2H, d of d, J=7, 10), 10.08 (1H, s). m.p. 165-166° C.

Workup

  1. customhydrogenated on a Parr shaker overnight
  2. temperatureIn the morning, the pressure was increased again to 50 psi
  3. filtrationThe reaction mixture was filtered
  4. customto remove the catalyst
  5. washwashed through a bed of silica gel with a mixture of ethyl acetate and ethanol
  6. customto remove traces of nickel salts
  7. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-293c64b2d6b04b43804f0c5d6f10e764
Source dataset
uspto-grants-2001_07
Patent number
US06255322B1

Reaction notes

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