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

HRID 1957118Notes

Reaction equation

HRID 1957118 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 (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 700 mL). 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. 1H NMR (300 MHz, CDCl3) 2.28 (3H, s), 3.36 (2H, br s), 3.42 (2H, br s), 6.72 (1H, s).

Workup

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

Sources & evidence

ORD record
ord-ae4bce2de86e4278976505da7c9774b4
Source dataset
uspto-grants-1998_07
Patent number
US05783572

Reaction notes

Loading…