Pyridine → Methyl 2,6-dichloro-4-cyanobenzoate

HRID 2201803Notes

Reaction equation

HRID 2201803 reaction equation
[C:1]([C:4]1[CH:13]=[C:12]([Cl:14])[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([Cl:15])[CH:5]=1)(=O)[NH2:2].N1C=CC=CC=1>>[Cl:14][C:12]1[CH:13]=[C:4]([C:1]#[N:2])[CH:5]=[C:6]([Cl:15])[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

3

Reactant 2

HCID 1049PyridineHCID 67128947Methyl 4-carbamoyl-2,6-dichlorobenzoate

Product 1

HCID 53401291Methyl 2,6-dichloro-4-cyanobenzoateYield 88%

Procedure

To a solution of methyl 4-carbamoyl-2,6-dichlorobenzoate (100 mg, 0.4 mmol) in pyridine (2 mL) trifluoro-acetic anhydride (0.11 ml, 0.8 mmol) was added drop wise at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 1 hour. The contents were poured into ice cold water and the precipitated solid was filtered, washed with water and dried to yield methyl 2,6-dichloro-4-cyanobenzoate (55 mg, 88%) as an off-white solid.

Workup

  1. additionThe contents were poured into ice cold water
  2. filtrationthe precipitated solid was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-cdc5d0a09c8440c083679e1d0224347f
Source dataset
uspto-grants-2016_06
Patent number
US09364466B2

Reaction notes

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