Stannous Chloride → HCID 86672143, compound

HRID 1842888Notes

Reaction equation

HRID 1842888 reaction equation
[Cl:1][C:2]1[C:3]([O:9][CH3:10])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[N:11]([O-])=O.[Na+].Cl[Sn]Cl>Cl.O>[Cl:1][C:2]1[C:3]([O:9][CH3:10])=[C:4]([NH:5][NH2:11])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 24479Stannous ChlorideHCID 142816Aniline, 3-chloro-2-methoxy-HCID 23668193Sodium Nitrite

Product 1

HCID 86672143HCID 86672143, compoundYield 110.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

To a stirred suspension of 3-chloro-2-methoxyaniline (5 g, 31.7 mmol, 1.0 eq) in conc. HCl (25 mL) was added a solution of NaNO2 (3.28 g, 47.55 mmol, 1.5 eq.) in water (5 mL) dropwise at −5 to 0° C. until the reaction mixture formed a clear solution. The reaction mixture was added drop wise to a stirred solution of SnCl2 (13.24 g, 69.74 mmol, 2.2 eq) in conc. HCl (50 mL) at −5° C. for 30 min. A solid precipitate obtained was filtered out and washed with excess of ice cold water to get (3-chloro-2-methoxyphenyl)hydrazine (6.049 g, 94%, brown solid; TLC system: EtOAc/PE (3:7) Rf: 0.4).

Workup

  1. customformed a clear solution
  2. customA solid precipitate obtained
  3. filtrationwas filtered out
  4. washwashed with excess of ice cold water

Sources & evidence

ORD record
ord-cbce46e1c5d34a8198e11cbc6726f46f
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

Loading…