Lithium Hydroxide → 453565-73-6

HRID 2216760Notes

Reaction equation

HRID 2216760 reaction equation
C[O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([N:10]([CH3:12])[CH3:11])[CH:7]=[C:6]([C:13]#[N:14])[CH:5]=1.[OH-].[Li+]>O1CCCC1>[C:13]([C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([N:10]([CH3:12])[CH3:11])[CH:7]=1)[C:3]([OH:15])=[O:2])#[N:14]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 21942414HCID 21942414, compound

Product 1

HCID 21942645453565-73-6Yield 101.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of methyl-3-cyano-5-dimethylaminobenzoate (318 mg, 1.6 mmol) in tetrahydrofuran (5 mL) was treated with 0.5 N lithium hydroxide (3.7 mL, 1.9 mmol). The reaction was stirred at 70° C. for 30 minutes and then the solvent was removed in vacuo. The residue was dissolved in a small amount of water and then acidified by the dropwise addition of 2 N hydrogen chloride until a white precipitate no longer formed. Following extraction of the aqueous layer with diethyl ether, the organic layer was then washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford 308 mg (quantitative) of 3-cyano-5-dimethylaminobenzoic acid.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in a small amount of water
  3. additionacidified by the dropwise addition of 2 N hydrogen chloride until a white precipitate
  4. customno longer formed
  5. extractionextraction of the aqueous layer with diethyl ether
  6. washthe organic layer was then washed with water and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9eb2409ae9534c73b9bfe4eb1b37c9f2
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

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