Stannous chloride dihydrate → 3-Hydrazino-4-methylbenzoic acid hydrochloride

HRID 565814

Reaction equation

HRID 565814 reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:9]([OH:11])=[O:10].O.O.[Cl:18][Sn]Cl>O.Cl.CC(O)=O>[ClH:18].[NH:5]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:9]([OH:11])=[O:10])[NH2:1]

Participants

7

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 755683-Amino-4-methylbenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 567775083-Hydrazino-4-methylbenzoic acid hydrochloride

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2.74 g of NaNO2 in 28 ml of water is added over 30 minutes to a solution, cooled to −5° C., of 5 g of 3-amino-4-methylbenzoic acid in 120 ml of concentrated HCl and 40 ml AcOH, and the mixture is left stirring for 1 hour 20 minutes at 0° C. After cooling to −10° C., a solution of 27.6 g of SnCl2.2H2O in 28 ml of concentrated HCl is added slowly. After stirring for 1 hour at RT, filtration, washing of the precipitate with 5 ml of 1N HCl and drying over P2O5 under vacuum, 6.15 g of the expected product are obtained.

Workup

  1. waitthe mixture is left
  2. temperatureAfter cooling to −10° C.
  3. stirringAfter stirring for 1 hour at RT
  4. filtrationfiltration
  5. washwashing of the precipitate with 5 ml of 1N HCl
  6. dry with materialdrying over P2O5 under vacuum, 6.15 g of the expected product
  7. customare obtained

Sources & evidence

ORD record
ord-d83664c365c444afb641f6b5767af214
Source dataset
uspto-grants-2001_01
Patent number
US06172239B2

Linked notes

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