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

HRID 1696466Notes

Reaction equation

HRID 1696466 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-aminophenyl)propionic acid ethyl ester (14 g, 72.5 mmol) in conc. HCl (200 mL) was added aqueous (10 mL) 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 conc. 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 EtOH and ether to yield 3-(3-hydrazinophenyl)propionic acid ethyl ester as a white solid, which was used for the next reaction without further purification. MS (ESI): m/z: 209 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-6c494c2c29aa4e61996ba79649405096
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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