2-Propenoic acid, 3-(4-nitrophenyl)- → 3-(4-Aminophenyl)prop-2-enoic acid

HRID 1253251Notes

Reaction equation

HRID 1253251 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.Cl.O1CCOCC1>C(O)(=O)C.O1CCCC1.[Zn]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:13][CH:14]=1

Participants

6

Reactant 2

HCID 701562-Propenoic acid, 3-(4-nitrophenyl)-HCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 929283-(4-Aminophenyl)prop-2-enoic acidYield 272.6%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

Cyclobranyl ester of p-nitrocinnamic acid (165.0 g, 0.268 mole) prepared according to the procedure of Example 103 was suspended in a mixture of acetic acid (1.5 l) and tetrahydrofuran (2 l). To the suspension were added 6N-HCl-dioxane (125 ml) and zinc powder (165 g) and the mixture was stirred at 20° C. for 2 hours. Then the reaction mixture was filtered to remove zinc powder. The filtrate was concentrated under reduced pressure, and the residue was extracted with chloroform. The extracts were washed successively with water and saturated aqueous NaHCO3, then dried, and concentrated in vacuo. The residual crystals were recrystallized from chloroform-ethanol (1:3, v/v), giving cyclobranyl ester of p-aminocinnamic acid (119.2 g), in a 75.9% yield. m.p. 206°-207° C.

Workup

  1. filtrationThen the reaction mixture was filtered
  2. customto remove zinc powder
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. extractionthe residue was extracted with chloroform
  5. washThe extracts were washed successively with water and saturated aqueous NaHCO3
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe residual crystals were recrystallized from chloroform-ethanol (1:3

Sources & evidence

ORD record
ord-32f70bed307d47dcad7d76e9f1f33371
Source dataset
uspto-grants-1988_05
Patent number
US04748161

Reaction notes

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