Potassium Hydroxide → p-[(E)-2-(1,2,3,4-tetrahydro-1,4-dimethyl-6-quinoxalinyl)propenyl]benzoic acid

HRID 1463423Notes

Reaction equation

HRID 1463423 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8](/[C:12](/[CH3:24])=[CH:13]/[C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=3)=[CH:9][CH:10]=2)[N:5]([CH3:25])[CH2:4][CH2:3]1.[OH-].[K+]>C(O)C.O>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8](/[C:12](/[CH3:24])=[CH:13]/[C:14]3[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)=[CH:9][CH:10]=2)[N:5]([CH3:25])[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67783456methyl p-[(E)-2-(1,2,3,4-tetrahydro-1,4-dimethyl-6-quinoxalinyl)propenyl]-benzoate

Product 1

HCID 67591124p-[(E)-2-(1,2,3,4-tetrahydro-1,4-dimethyl-6-quinoxalinyl)propenyl]benzoic acidYield 78.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

600 mg of this ester were converted into the free acid by reaction with a solution of 1.5 g of potassium hydroxide in 25 ml of ethanol and 10 ml of water at 50° C. during 4 hours. After recrystallization from ethyl acetate/hexane, there were obtained 450 mg of p-[(E)-2-(1,2,3,4-tetrahydro-1,4-dimethyl-6-quinoxalinyl)propenyl]benzoic acid in the form of orange crystals, melting point 203°-205° C.

Workup

  1. customAfter recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d4d3c7df66e047fea4159cceffc19fa6
Source dataset
uspto-grants-1994_04
Patent number
US05300522

Reaction notes

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