Sodium Hydroxide → 3-Fluoro-2-iodophenylhydrazine Hydrochloride

HRID 620716Notes

Reaction equation

HRID 620716 reaction equation
[ClH:1].[I:2][C:3]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].[N:11]([O-])=O.[Na+].[OH-].[Na+]>Cl.O>[ClH:1].[F:10][C:9]1[C:3]([I:2])=[C:4]([NH:5][NH2:11])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 200290923-Fluoro-2-iodoaniline hydrochlorideHCID 23668193Sodium Nitrite

Product 1

HCID 200290893-Fluoro-2-iodophenylhydrazine Hydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
-10 °C

Procedure

2-Iodo-3-fluoroaniline hydrochloride (5.7 g, 0.021 mol) was stirred in 7.4 mL of concentrated HCl and cooled to -10° C. An aqueous solution of sodium nitrite (1.63 g, 0.024 mL) in 5 mL water was added dropwise over a 20 minute period, stannous chloride (9.95 g, 0.044 mol) in 12 mL of 6N HCl added at -5° C., warmed to room temperature and stirring continued for 4 hours. The reaction mixture was cooled to 0° C., and made basic with 50% NaOH (pH 10-11), extracted with ether, washed with water, brine, dried (MgSO4), filtered and concentrated to give the hydrazine. Addition of ethereal HCl (pH 1-2) gave 4.6 g of the title compound, m.p. 165°-167° C.

Workup

  1. temperaturewarmed to room temperature
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. extractionextracted with ether
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-88b0f6ba1f934498a143d1bfffc8d64b
Source dataset
uspto-grants-1989_04
Patent number
US04822781

Reaction notes

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