Malonic Acid → 2-Nitro-5-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]cinnamic acid

HRID 1649200Notes

Reaction equation

[N+:1]([C:4]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([C:18](=[O:29])[C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=3)[CH2:14][CH2:13]2)=[CH:8][C:5]=1C=O)([O-:3])=[O:2].[C:30](O)(=O)[CH2:31][C:32]([OH:34])=[O:33].N1CCCCC1>N1C=CC=CC=1>[N+:1]([C:4]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([C:18](=[O:29])[C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=3)[CH2:14][CH2:13]2)=[CH:8][C:5]=1[CH:30]=[CH:31][C:32]([OH:34])=[O:33])([O-:3])=[O:2]

Participants

Conditions

Temperature: 80 °C

Procedure

2-Nitro-5-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]benzaldehyde (4 g) was dissolved in 20 ml of pyridine followed by adding 2.1 g of malonic acid and 0.4 ml of piperidine, and the mixture was stirred at 80° C. for 4 hours. After evaporating pyridine and piperidine the reaction mixture was poured in a dilute aqueous hydrogen chloride solution and extracted with methylene chloride. After washing the methylene chloride layer with water the solvent was distilled off and methanol was added to the residue. After cooling, crystals which formed were collected by filtration to give 3.7 g of 2-nitro-5-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-cinnamic acid, m.p. 197°-202° C.

Workup

customAfter evaporating pyridine and piperidine the reaction mixture
additionwas poured in a dilute aqueous hydrogen chloride solution
extractionextracted with methylene chloride
washAfter washing the methylene chloride layer with water the solvent
distillationwas distilled off
additionmethanol was added to the residue
temperatureAfter cooling
customcrystals which formed
filtrationwere collected by filtration

Sources & evidence

ORD record: ord-582ee681d2e746ebbb96c318c37f36d6
Source dataset: uspto-grants-1983_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04415572

Reaction notes

Loading…