3-Aminobenzoic Acid → 3-Hydrazinobenzoic acid hydrochloride
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[N:11]([O-])=O.[Na+].O.O.[Cl:17][Sn]Cl>Cl>[ClH:17].[NH:1]([C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6])[NH2:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution (200 mL) of m-amino benzoic acid (200 g, 1.46 mol) in concentrated HCl was added an aqueous solution (250 mL) of NaNO2 (102 g, 1.46 mol) at 0° C. The reaction mixture was stirred for 1 h and a solution of SnCl2.2H2O (662 g, 2.92 mol) in concentrated HCl (2L) was then added at 0° C., and the reaction stirred for an additional 2 h at RT. The precipitate was filtered and washed with ethanol and ether to yield 3-hydrazino-benzoic acid hydrochloride as a white solid.
Workup
- stirringthe reaction stirred for an additional 2 h at RT
- filtrationThe precipitate was filtered
- washwashed with ethanol and ether
Sources & evidence
- ORD record
- ord-fc84a7d95e2c4e30b2b63bd4efd1c754
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07737283B2
Reaction notes
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