Stannous Chloride → 3-Hydrazino-4-methylbenzoic acid hydrochloride

HRID 1723951Notes

Reaction equation

HRID 1723951 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[N:12]([O-])=O.[Na+].[Cl:16][Sn]Cl>Cl.O>[ClH:16].[NH:1]([C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6])[NH2:12]

Participants

6

Reactant 3

HCID 24479Stannous ChlorideHCID 755683-Amino-4-methylbenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 567775083-Hydrazino-4-methylbenzoic acid hydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

To a suspension of 3-amino-4-methylbenzoic acid (5.0 g, 33 mmol) in concentrated HCl (31 mL) cooled to below −5 ° C. was added a solution of NaNO2 (2.4 g, 35 mmol) in water (12 mL) at such rate that the temperature remained below −4 ° C. After stirring for 45 min, the suspension was transferred to a cold stirred solution of SnCl2 (28 g, 124 mmol) in concentrated HCl (18 mL) via pipette. The resulting solid was collected via vacuum filtration and washed first with cold water and then with Et2O. The solid was recrystallized from water/2-propanol (10:1) to provide 3-hydrazino-4-methyl-benzoic acid hydrochloride. (2.23 g, 33%) as a pink solid. ESI MS m/z 167 [C8H10N2O2+H]+.

Workup

  1. temperaturecooled to below −5 ° C.
  2. customremained below −4 ° C
  3. filtrationThe resulting solid was collected via vacuum filtration
  4. washwashed first with cold water
  5. customThe solid was recrystallized from water/2-propanol (10:1)

Sources & evidence

ORD record
ord-39954e03a9ba445fa9297505196470a4
Source dataset
uspto-grants-2009_02
Patent number
US07485657B2

Reaction notes

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