Ethyl 3-aminobenzoate → Ethyl 3-hydrazinylbenzoate

HRID 1696597Notes

Reaction equation

HRID 1696597 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[CH:6]=1)[CH3:2].[N:13]([O-])=O.[Na+].O.O.Cl[Sn]Cl>Cl>[NH:11]([C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:12])[NH2:13]

Participants

5

Reactant 3

HCID 11400Ethyl 3-aminobenzoateHCID 61436Stannous chloride dihydrateHCID 23668193Sodium Nitrite

Product 1

HCID 21701845Ethyl 3-hydrazinylbenzoate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

To a solution of m-aminobenzoic acid ethyl ester (200 g, 1.21 mmol) in conc. HCl (200 mL) was added an aqueous solution (250 mL) of NaNO2 (102 g, 1.46 mmol) at 0° C. and the reaction mixture was stirred for 1 h. A solution of SnCl2.2H2O (662 g, 2.92 mmol) in conc. HCl (2 L) was then added at 0° C. The reaction solution was stirred for 2 h at RT. The precipitate was filtered and washed with ethanol and ether to yield ethyl 3-hydrazinobenzoate, which was used for the next reaction without further purification.

Workup

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

Sources & evidence

ORD record
ord-191928e917ba465280dbf8b33fd23fed
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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