Hydrochloric Acid → (4-Bromo-3-methylphenyl)hydrazine hydrochloride

HRID 1993763Notes

Reaction equation

HRID 1993763 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].[N:10]([O-])=O.[Na+].[ClH:14]>>[ClH:14].[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][NH2:10])=[CH:4][C:3]=1[CH3:9]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 233594-Bromo-3-methylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 16495351(4-Bromo-3-methylphenyl)hydrazine hydrochloride

Conditions

Temperature
0 °C

Procedure

4-Bromo-3-methylaniline (10.2 g) was suspended in 6N HCl (85 mL) and cooled to 0° C. A solution of sodium nitrite (4 g in 40 mL H2O) was added over 10 min. The reaction was stirred for 15 min at 0° C. followed by the addition of stannous chloride dihydrate (36 g in 25 mL 12N HCl). The reaction was stirred for 2 hours at 0° C. The reaction was filtered, and the filter cake was washed with cold H2O to afford 4-bromo-3-methylphenylhydrazine hydrochloride (compound 2a, 20 g) as a tan solid.

Workup

  1. stirringThe reaction was stirred for 2 hours at 0° C
  2. filtrationThe reaction was filtered
  3. washthe filter cake was washed with cold H2O

Sources & evidence

ORD record
ord-7e734484e5624172abd33b1974579260
Source dataset
uspto-grants-2010_01
Patent number
US07652035B2

Reaction notes

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