3-(2-Nitrophenyl)acrylic acid → Hydrocarbostyril

HRID 414551Notes

Reaction equation

HRID 414551 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.[Pd]>[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 64796Hydrocarbostyril

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 25 g of o-nitrocinnamic acid in 250 ml of ethanol was shaken with 2.5 g of 10% palladium on carbon under hydrogen at a pressure of 3 atmospheres. When the theoretical amount of hydrogen had been absorbed the catalyst was filtered off, washed with hot ethanol and the filtrate evaporated under reduced pressure to give 3,4-dihydrocarbosytril, m.p. 168°-169° C.

Workup

  1. customWhen the theoretical amount of hydrogen had been absorbed the catalyst
  2. filtrationwas filtered off
  3. washwashed with hot ethanol
  4. customthe filtrate evaporated under reduced pressure
  5. customto give 3,4-dihydrocarbosytril

Sources & evidence

ORD record
ord-5ddb15b8e8ef4e80b242fcfb9689bd83
Source dataset
uspto-grants-1988_12
Patent number
US04792561

Reaction notes

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