2,3-Dimethylaniline → 6-Chloro-2,3-dimethylaniline

HRID 1977649

Reaction equation

HRID 1977649 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:11]=1[NH2:12]>CN(C=O)C>[CH3:9][C:10]1[C:16]([CH3:17])=[CH:15][CH:14]=[C:13]([Cl:1])[C:11]=1[NH2:12]

Participants

4

Reactant 2

HCID 68932,3-DimethylanilineHCID 31398Chlorosuccinimide

Product 1

HCID 219947436-Chloro-2,3-dimethylanilineYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

used in the preparation of 389 was prepared as follows: N-Chlorosuccinimide (1.00 g; 8.2 mmol) was added to a solution of 2,3-dimethylaniline (1 ml; 8.2 mmol) in 20 ml of DMF in the dark. After stirring 1 hr. in the dark, the reaction mixture was partitioned between EtOAc (100 ml) and water (100 ml). The organic layer was washed with 1N NaOH (100 ml), water (100 ml) and brine (50 ml). Drying (MgSO4) and concentration afforded 1.25 g (99%) of 2,3-dimethyl-6-chloroaniline as a deep red liquid.

Workup

  1. customwas prepared
  2. customin the dark, the reaction mixture was partitioned between EtOAc (100 ml) and water (100 ml)
  3. washThe organic layer was washed with 1N NaOH (100 ml), water (100 ml) and brine (50 ml)
  4. customDrying
  5. concentration(MgSO4) and concentration

Sources & evidence

ORD record
ord-b0cb638d6a32473e867ac1465c30ef9d
Source dataset
uspto-grants-2001_05
Patent number
US06235740B1

Linked notes

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