Stannous chloride dihydrate → HCID 10375773, compound

HRID 1696470Notes

Reaction equation

HRID 1696470 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][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:8]=[CH:9][C:10]([NH:13][NH2:15])=[CH:11][CH:12]=1)[CH3:2]

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 10442595Ethyl 3-(4-aminophenyl)propanoateHCID 23668193Sodium Nitrite

Product 1

HCID 10375773HCID 10375773, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

To a solution of 3-(4-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 Et2O to yield 3-(4-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 Et2O

Sources & evidence

ORD record
ord-85e53f167e8e423295c0d2f3c4d02ff3
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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