Ethanol → 2-Nitro-5-piperazinylcinnamic acid ethyl ester hydrochloride

HRID 1649198Notes

Reaction equation

HRID 1649198 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:11][C:5]=1[CH:6]=[CH:7][C:8]([OH:10])=[O:9])([O-:3])=[O:2].S(Cl)([Cl:23])=O.[CH2:25](O)[CH3:26]>>[ClH:23].[CH2:25]([O:9][C:8](=[O:10])[CH:7]=[CH:6][C:5]1[CH:11]=[C:12]([N:15]2[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]2)[CH:13]=[CH:14][C:4]=1[N+:1]([O-:3])=[O:2])[CH3:26]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 570123252-Nitro-5-piperazinylcinnamic acid

Product 1

HCID 705346722-Nitro-5-piperazinylcinnamic acid ethyl ester hydrochloride

Procedure

2-Nitro-5-piperazinylcinnamic acid (10 g) was suspended in 100 ml of ethyl alcohol and to the suspension was added dropwise 3 ml of thionyl chloride with ice cooling externally while stirring. After completion of addition, the mixture was heated under reflux for 3 hours and ethyl alcohol and thionyl chloride were removed by distillation. The residue was added to isopropyl alcohol and heated to dissolve. After cooling, yellow crystals which precipitated were collected by filtration to give 4.3 g of 2-nitro-5-piperazinylcinnamic acid ethyl ester hydrochloride, m.p. 210°-220° C.

Workup

  1. additionAfter completion of addition
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 3 hours
  4. customethyl alcohol and thionyl chloride were removed by distillation
  5. additionThe residue was added to isopropyl alcohol
  6. temperatureheated to dissolve
  7. temperatureAfter cooling
  8. customyellow crystals which precipitated
  9. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-75c8360314114a92828202a4279dcfbb
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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