3-Aminobenzoic Acid → 3-Hydrazinobenzoic acid hydrochloride

HRID 857134

Reaction equation

HRID 857134 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

HCID 74193-Aminobenzoic AcidHCID 61436Stannous chloride dihydrateHCID 23668193Sodium Nitrite

Product 1

HCID 128918633-Hydrazinobenzoic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

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 (2 L) 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

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

Sources & evidence

ORD record
ord-645793c269594b1e94d3122f95c70ae3
Source dataset
uspto-grants-2006_12
Patent number
US07144911B2

Linked notes

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