Sodium Hydroxide → HCID 22217750, compound

HRID 431538Notes

Reaction equation

HRID 431538 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([NH2:9])[CH:5]=[CH:6][C:7]=1[CH3:8].[N:10]([O-])=O.[Na+].O.O.[Sn](Cl)Cl.[OH-].[Na+]>Cl.O>[I:1][C:2]1[CH:3]=[C:4]([NH:9][NH2:10])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 1188893-Iodo-p-toluidineHCID 23668193Sodium Nitrite

Product 1

HCID 22217750HCID 22217750, compoundYield 67.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

3-Iodo-4-methylphenyl amine (10 g, 43 mmol) was dissolved in 6 N HCl (40 ML), cooled to 0° C., and vigorously stirred throughout the procedure. Sodium nitrite (2.9 g, 1.03 equiv.) was dissolved in water (5 mL) and this solution was added to the reaction in a dropwise fashion. After 30 min, tin (II) chloride dihydrate (22.8 g, 1 mol) in 6 N HCl (100 mL) was added via addition funnel, and the reaction slurry was stirred at 0° C. for 3 h. The pH was adjusted to 14 with 40% aqueous sodium hydroxide solution and the aqueous mixture was extracted with EtOAc, (6×50 mL), dried (MgSO4), and concentrated to give 3-iodo-4-methylphenylhydrazine (7 g, 57%). This material was used directly without further purification.

Workup

  1. additionthis solution was added to the reaction in a dropwise fashion
  2. stirringthe reaction slurry was stirred at 0° C. for 3 h
  3. extractionthe aqueous mixture was extracted with EtOAc, (6×50 mL),
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2439464c70d945a08e635b5b6db3e3b4
Source dataset
uspto-grants-2003_12
Patent number
US06660732B2

Reaction notes

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