Sodium Hydroxide → 2,4-Dichloro-m-toluidine

HRID 1732636Notes

Reaction equation

HRID 1732636 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[CH3:12].[OH-].[Na+]>Cl.C(O)C>[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([Cl:11])[CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 971552,6-Dichloro-3-nitrotoluene

Product 1

HCID 882822,4-Dichloro-m-toluidineYield 78.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A stirred solution of 50.0 g (0.243 mole) of 2,6-dichloro-3-nitrotoluene and 225 g (1.0 mole) of stannous chloride in 250 ml of concentrated hydrochloric acid and 125 ml of ethanol was heated under reflux for 1 hour. The reaction mixture was allowed to cool to ambient temperature and was stirred for 16 hours, made basic with sodium hydroxide, and concentrated under reduced pressure. The residue was slurried with water and the insolubles were collected by filtration and allowed to air dry. The solid was digested with 500 ml of chloroform and 100 ml of ethanol. The mixture was filtered and the filtrate concentrated under reduced pressure to give 33.5 g of 2,4-dichloro-3-methylaniline, m.p. 56°-57.5° C. The nmr spectrum was consistent with the proposed structure.

Workup

  1. temperatureunder reflux for 1 hour
  2. concentrationconcentrated under reduced pressure
  3. filtrationthe insolubles were collected by filtration
  4. customto air dry
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-79c83c9fcc674a45b0fa1636c8326aae
Source dataset
uspto-grants-1980_12
Patent number
US04238505

Reaction notes

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