Stannous Chloride → Ethyl 2-chloro-5-hydrazinocinnamate

HRID 48497Notes

Reaction equation

HRID 48497 reaction equation
[Sn](Cl)Cl.[NH2:4][C:5]1[CH:6]=[CH:7][C:8]([Cl:18])=[C:9]([CH:17]=1)[CH:10]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].[N:19]([O-])=O.[Na+]>Cl>[Cl:18][C:8]1[CH:7]=[CH:6][C:5]([NH:4][NH2:19])=[CH:17][C:9]=1[CH:10]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 23668193Sodium NitriteHCID 54425193Ethyl 5-amino-2-chlorocinnamate

Product 1

HCID 54155293Ethyl 2-chloro-5-hydrazinocinnamateYield 34.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

First, 60 g of tin(II)chloride was dissolved in 60 ml of concentrated hydrochloric acid, and the mixture was cooled to −30° C., to which a diazonium solution prepared from 19 g of ethyl 5-amino-2-chlorocinnamate and 6.3 g of sodium nitrite was added dropwise at 0° C. or lower. The reaction mixture was stirred at room temperature for 1 hour, and the precipitated crystals were collected by filtration. These crystals were added to ice-water, neutralized with 2N aqueous sodium hydroxide, and extracted with chloroform. The chloroform layer was dried and concentrated, which afforded 7.0 g of ethyl 2-chloro-5-hydrazinocinnamate.

Workup

  1. additionwas added dropwise at 0° C.
  2. filtrationthe precipitated crystals were collected by filtration
  3. additionThese crystals were added to ice-water
  4. extractionextracted with chloroform
  5. dry with materialThe chloroform layer was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3abeb261181749c1a1f15bb4932c7ff0
Source dataset
uspto-grants-2004_03
Patent number
US06703503B2

Reaction notes

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