Sodium Dithionite → 2,3-Diamino-5,6-dichlorotoluene

HRID 1458590Notes

Reaction equation

HRID 1458590 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[NH2:9][C:10]1[C:11]([N+:19]([O-])=O)=[C:12]([CH3:18])[C:13]([Cl:17])=[C:14]([Cl:16])[CH:15]=1.C(=O)(O)[O-].[K+]>O.CO>[NH2:19][C:11]1[C:10]([NH2:9])=[CH:15][C:14]([Cl:16])=[C:13]([Cl:17])[C:12]=1[CH3:18]

Participants

6

Reactant 3

HCID 24489Sodium DithioniteHCID 516893Potassium BicarbonateHCID 104210423-Amino-5,6-dichloro-2-nitrotoluene

Product 1

HCID 106077272,3-Diamino-5,6-dichlorotolueneYield 75.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium dithionite (94 g, 0.54 mol) in water (1 L) was added to a stirred mixture of 3-amino-5,6-dichloro-2-nitrotoluene (from step (b), 39.7 g, 0.18 mol) and potassium bicarbonate (94 g, 0.94 mmol) in methanol (1 L) at room temperature. After 30 minutes, the mixture was concentrated under reduced pressure and the resulting suspension extracted with ethyl acetate (total of 700mi). The extracts were dried (MgSO4) and concentrated under reduced pressure to give 2,3-diamino-5,6-dichlorotoluene (26.1 g, 38% over 2 steps) as a brown solid.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. extractionthe resulting suspension extracted with ethyl acetate (total of 700mi)
  3. dry with materialThe extracts were dried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9896292a6c75418cab516e9fb9506f16
Source dataset
uspto-grants-1998_12
Patent number
US05852016

Reaction notes

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