Stannous Chloride → HCID 18540678, compound

HRID 1860568Notes

Reaction equation

HRID 1860568 reaction equation
[NH2:1][C:2]1[C:12]([Cl:13])=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[Cl:14].[N:15]([O-])=O.[Na+].[Sn](Cl)Cl>Cl.O>[ClH:13].[Cl:14][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([Cl:13])[C:2]=1[NH:1][NH2:15])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

6

Reactant 3

HCID 24479Stannous ChlorideHCID 99328Ethyl 4-amino-3,5-dichlorobenzoateHCID 23668193Sodium Nitrite

Product 1

HCID 18540678HCID 18540678, compoundYield 107.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Part A: To a stirred suspension of 4.33 g (18.5 mmol) of ethyl 4-amino-3,5-dichlorobenzoate in 8 mL conc. HCl at 0° C. was added a solution of 1.28 g (18.5 mmol) of sodium nitrite in 8 mL water dropwise. After stirring at 0° C. for 45 min, a solution of 12.52 g (55.5 mmol) tin(II) chloride in 14 mL conc. HCl was added dropwise. The reaction was sealed and placed in the refrigerator for 18 h. The solid was collected by suction filtration, washed with brine and then 2:1 petroleum ether-diethyl ether, treated with 1 N NaOH, and filtered. This solid was dissolved in diethyl ether, acidified with 4 N HCl in dioxane, filtered and washed with diethyl ether to give 2.85 g (54%) of ethyl 3,5-dichloro-4-hydrazinobenzoate hydrochloride, mp 225-227 (dec)° C. Mass Spec.: (CI+) 249 (M+).

Workup

  1. customThe reaction was sealed
  2. waitplaced in the refrigerator for 18 h
  3. filtrationThe solid was collected by suction filtration
  4. washwashed with brine
  5. addition2:1 petroleum ether-diethyl ether, treated with 1 N NaOH
  6. filtrationfiltered
  7. dissolutionThis solid was dissolved in diethyl ether
  8. filtrationfiltered
  9. washwashed with diethyl ether

Sources & evidence

ORD record
ord-d6964e3c53354311b1aca7a1ff483a17
Source dataset
uspto-grants-2003_03
Patent number
US06531477B1

Reaction notes

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