Hydrochloric Acid → (3-Cyano-4-methoxyphenyl)hydrazine hydrochloride

HRID 429322Notes

Reaction equation

HRID 429322 reaction equation
[N:1]([O-])=O.[Na+].[C:5]([C:7]1[CH:8]=[C:9]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[NH2:10])#[N:6].Cl.O.O.[Sn](Cl)[Cl:20]>O>[ClH:20].[C:5]([C:7]1[CH:8]=[C:9]([NH:10][NH2:1])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15])#[N:6]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 61436Stannous chloride dihydrateHCID 41026715-Amino-2-methoxybenzonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 18355391(3-Cyano-4-methoxyphenyl)hydrazine hydrochlorideYield 142.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of sodium nitrite (4.0 g) in water (7 ml) was added to an ice cooled mixture of 3-cyano-4-methoxyaniline (7.7 g) and concentrated hydrochloric acid (21 ml). The mixture was stirred at 0° C. for 30 minutes. To the resultant mixture a solution of tin(II) chloride dihydrate (49 g) and concentrated hydrochloric acid (5 ml) was added at 0° C. and stirred for 1 hour. The precipitates were filtered and washed with ice cooled concentrated hydrochloric acid (10 ml) to give crude (3-cyano-4-methoxyphenyl)hydrazine hydrochloride (14.8 g).

Workup

  1. temperaturecooled
  2. stirringstirred for 1 hour
  3. filtrationThe precipitates were filtered
  4. washwashed with ice
  5. temperaturecooled concentrated hydrochloric acid (10 ml)

Sources & evidence

ORD record
ord-b6fd74e26a264987a673f11046a3f5ad
Source dataset
uspto-grants-2001_11
Patent number
US06316485B1

Reaction notes

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