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

HRID 1253250Notes

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.O1CCOCC1.[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

Conditions

Temperature: 40 °C

Procedure

Cycloartenyl ester of p-nitro cinnamic acid (160.0 g, 0.266 mole) prepared according to the procedure of Example 101 was suspended in a mixture of acetic acid (1.5 l) and dioxane (1.5 l). To the suspension were added 6N-HCl-dioxane (95 ml) and zinc powder (80 g) and the mixture was stirred at 40° C. for 3 hours. After the reaction, zinc powder was removed by filtration. 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 under reduced pressure. The residual crystals were recrystallized from chloroform-ethanol (1:5, v/v), giving cycloartenyl ester of p-aminocinnamic acid (140.0 g), in a 92.0% yield. m.p. 185°-187° C.

Workup

customwas removed by filtration
concentrationThe filtrate was concentrated under reduced pressure
extractionthe residue was extracted with chloroform
washThe extracts were washed successively with water and saturated aqueous NaHCO3
customdried
concentrationconcentrated under reduced pressure
customThe residual crystals were recrystallized from chloroform-ethanol (1:5

Sources & evidence

ORD record: ord-b888d9c3d2e442969f1cfb77aa7977e2
Source dataset: uspto-grants-1988_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04748161

Reaction notes

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