p-(p-Chlorocinnamamido)benzoic acid, ethyl ester → HCID 13503432, compound

HRID 485248Notes

Reaction equation

HRID 485248 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH:6]=[CH:7][C:8]([NH:10][C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=2)=[O:9])=[CH:4][CH:3]=1.[H][H]>[Pd].O1CCCC1>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][CH2:7][C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:20][CH:21]=2)=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 692488p-(p-Chlorocinnamamido)benzoic acid, ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 13503432HCID 13503432, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 30.0 g. of 4-(p-chlorocinnamamido)benzoic acid, ethyl ester, 500 mg. of 10% palladium on carbon, and 150 ml. of tetrahydrofuran is hydrogenated in a Parr apparatus, over a 2 hour period, repressurizing until hydrogen uptake is complete. The mixture is filtered, and the filtrate is evaporated. The solid is crystallized from 175 ml. of ethanol, giving 26.8 g. of the desired product as white crystals, m.p. 163°-165° C.

Workup

  1. additionA mixture of 30.0 g
  2. filtrationThe mixture is filtered
  3. customthe filtrate is evaporated
  4. customThe solid is crystallized from 175 ml
  5. customof ethanol, giving 26.8 g

Sources & evidence

ORD record
ord-3faf2a09773d453fb8666c6fc6dcaa3f
Source dataset
uspto-grants-1985_08
Patent number
US04536346

Reaction notes

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