Hydrochloric Acid → 3-Chloro-2-cyanobenzoic acid

HRID 421994Notes

Reaction equation

HRID 421994 reaction equation
C[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([C:11]#[N:12])[C:3]=1[Cl:13].[OH-].[Na+].Cl>CO>[Cl:13][C:3]1[C:4]([C:11]#[N:12])=[C:5]([CH:9]=[CH:10][CH:2]=1)[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66676571Methyl 3-chloro-2-cyanobenzoic acid

Product 1

HCID 533972953-Chloro-2-cyanobenzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixture of 430 mg of methyl 3-chloro-2-cyanobenzoic acid obtained by the same manner as in U.S. Pat. No. 4,900,739, 22 ml of methanol and 2.5 ml of aqueous sodium hydroxide (1 mol/l) was stirring at room temperature for 2 hours. To the reaction mixture was added hydrochloride (5 mol/l) and was extracted with chloroform. The organic layer was washed with water and saturated brine, and then dried over magnesium sulfate. The organic layer was filtered and concentrated in vacuo to give the title compound.

Workup

  1. customobtained by the same manner as in U.S
  2. extractionwas extracted with chloroform
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe organic layer was filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bdf338e722c146889b2ab6f5cf116b09
Source dataset
uspto-grants-2012_01
Patent number
US08101621B2

Reaction notes

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