5-Amino-2-chlorobenzoic acid → 2-Chloro-5-hydrazinylbenzoic acid hydrochloride

HRID 565813

Reaction equation

HRID 565813 reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[CH:7]=[CH:8][C:9]([Cl:15])=[C:10]([CH:14]=1)[C:11]([OH:13])=[O:12].O.O.Cl[Sn]Cl>O.Cl>[ClH:15].[NH:5]([C:6]1[CH:7]=[CH:8][C:9]([Cl:15])=[C:10]([CH:14]=1)[C:11]([OH:13])=[O:12])[NH2:1]

Participants

6

Reactant 3

HCID 378795-Amino-2-chlorobenzoic acidHCID 61436Stannous chloride dihydrateHCID 23668193Sodium Nitrite

Product 1

HCID 164957252-Chloro-5-hydrazinylbenzoic acid hydrochlorideYield 123.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
-3 °C

Procedure

A solution of 2.11 g of NaNO2 in 40 ml of water is added over 30 minutes to a suspension, cooled to −2° C., of 5 g of 5-amino-2-chlorobenzoic acid in 50 ml of concentrated HCl. The solution is stirred for 2 hours at −3° C. and cooled to −10° C., and a solution of 23 g of SnCl2.2H2O in 20 ml of concentrated HCl and 20 ml of water is added over 30 minutes. The mixture is stirred for one and a half hours at 0° C. and filtered, and the precipitate is dried to obtain 4 g of expected product.

Workup

  1. temperaturecooled to −10° C.
  2. stirringThe mixture is stirred for one and a half hours at 0° C.
  3. filtrationfiltered
  4. customthe precipitate is dried

Sources & evidence

ORD record
ord-fd6f079ef34b4c6a9e61fec9a095b282
Source dataset
uspto-grants-2001_01
Patent number
US06172239B2

Linked notes

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