2,3-Dimethylaniline → HCID 20512473, compound

HRID 1164445Notes

Reaction equation

HRID 1164445 reaction equation
[Cl:1][CH:2]([CH3:13])[CH2:3][NH:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:12].[CH3:14][C:15]1[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:16]=1[NH2:17]>[I-].[K+].C(O)(C)C>[ClH:1].[ClH:1].[CH3:12][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([CH3:11])[C:5]=1[NH:4][CH2:3][CH:2]([NH:17][C:16]1[CH:18]=[CH:19][CH:20]=[C:21]([CH3:22])[C:15]=1[CH3:14])[CH3:13]

Participants

5

Reactant 2

HCID 68932,3-DimethylanilineHCID 13674776HCID 13674776, compound

Product 1

HCID 20512473HCID 20512473, compoundYield 113.3%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of 29.5 g (0.15 moles) of N-(β-chloropropyl)-2,6-dimethyl-aniline, prepared as described in Example 3, Method (b), point (a), 37.2 ml (36.3 g, 0.3 moles) of 2,3-dimethylaniline and 0.5 g (3 mmoles) of potassium iodide is stirred at 100° to 105° C. for 3 hours under nitrogen atmosphere. The mixture is allowed to cool, admixed with 30 ml of isopropanol, the separated precipitate is filtered off, washed with cold isopropanol and dried. In this way 14.25 g (30.2%) of 2,3-dimethylaniline hydrochloride are separated. The filtrate is admixed with 200 ml of water, the mixture is acidified with 20% aqueous hydrochloric acid, the separated precipitate is filtered off, washed with water and dried. 30.2 g (56.7%) of 1-(2',6'-dimethylphenyl-amino)-2-(2',3'-dimethylphenyl-amino)-propane dihydrochloride are obtained. This salt is treated as described in Example 3, Method (b) point (c) to obtain the free base. The base is isolated by extracting the mixture with chloroform. The resulting substance is an oil at room temperature.

Workup

  1. customprepared
  2. temperatureto cool
  3. filtrationthe separated precipitate is filtered off
  4. washwashed with cold isopropanol
  5. customdried
  6. customIn this way 14.25 g (30.2%) of 2,3-dimethylaniline hydrochloride are separated
  7. filtrationthe separated precipitate is filtered off
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-ca7398cf0cd2497aa59c1b977c914c84
Source dataset
uspto-grants-1983_01
Patent number
US04369325

Reaction notes

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