Hydrochloric Acid → HCID 67049719, compound

HRID 885887Notes

Reaction equation

HRID 885887 reaction equation
[CH:1]([C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1)=O.[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[C:19]([C:21](=[O:23])[CH3:22])[CH:20]=1.[OH-].[K+].Cl>CCO>[ClH:14].[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[C:19]([C:21](=[O:23])/[CH:22]=[CH:1]/[C:3]2[CH:13]=[CH:12][C:6](/[CH:7]=[CH:8]/[C:9]([OH:11])=[O:10])=[CH:5][CH:4]=2)[CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 980772-Propenoic acid, 3-(4-formylphenyl)-HCID 58208385HCID 58208385, compound

Product 1

HCID 67049719HCID 67049719, compoundYield 163.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-formylcinnamic acid (397 mg, 2.25 mmol), 1-[5-chloro-2-(4-methyl-piperazin-1-yl)-phenyl]-ethanone (obtained as described in Preparation 10, 570 mg, 2.25 mmol) and 1.7 M KOH (2.66 ml) in EtOH (25 ml) was stirred at 0° C. for 3 h and then acidified with 10% HCl. The solution was concentrated until formation of a yellow precipitate. The solid was filtered to give 823 mg of (E)-3-(4-{(E)-3-[5-chloro-2-(4-methyl-piperazin-1-yl)-phenyl]-3-oxo-propenyl}-phenyl)-acrylic acid hydrochloride.

Workup

  1. concentrationThe solution was concentrated until formation of a yellow precipitate
  2. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-8e662c1b9295498eb66ff8f0f00ff72a
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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