Stannous chloride dihydrate → 3-(3-Hydrazinophenyl)propionic acid ethyl ester

HRID 16954Notes

Reaction equation

HRID 16954 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH2:13])[CH:8]=1)[CH3:2].[N:15]([O-])=O.[Na+].O.O.Cl[Sn]Cl>Cl>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][NH2:15])[CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 82314Ethyl 3-(3-Aminophenyl)propionateHCID 23668193Sodium Nitrite

Product 1

HCID 588429213-(3-Hydrazinophenyl)propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

To a solution of 3-(3-amino-phenyl)-propionic acid ethyl ester (14 g, 72.5 mmol) in concentrated HCl (200 mL) was added an aqueous solution (10 mL) of NaNO2 (5 g, 72.5 mmol) at 0° C. and the resulting mixture was stirred for 1 h. A solution of SnCl2.2H2O (33 g, 145 mmol) in concentrated HCl (150 mL) was then added at 0° C. The reaction solution was stirred for an additional 2 h at RT. The precipitate was filtered and washed with ethanol and ether to give 3-(3-hydrazino-phenyl)-propionic acid ethyl ester as a white solid, which was used without further purification.

Workup

  1. stirringThe reaction solution was stirred for an additional 2 h at RT
  2. filtrationThe precipitate was filtered
  3. washwashed with ethanol and ether

Sources & evidence

ORD record
ord-47fa71e0b53046b79ce413a9ccedfaaf
Source dataset
uspto-grants-2010_06
Patent number
US07737283B2

Reaction notes

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