Lithium Hydroxide → HCID 21942507, compound

HRID 431869Notes

Reaction equation

HRID 431869 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)[CH:11]=1)[C:6]([O-:8])=[O:7])#[N:2].[OH-].[Li+]>O1CCCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)[CH:11]=1)[C:6]([OH:8])=[O:7])#[N:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 21942670HCID 21942670, compound

Product 1

HCID 21942507HCID 21942507, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 3-cyano-5-(1H-imidazol-1-yl-methyl)benzoate (150 mg, 0.62 mmol) in tetrahydrofuran (2 mL) was treated with 0.5 N lithium hydroxide (1.5 mL, 0.75 mmol). The reaction was stirred at 70° C. for 10 minutes and then the solvent was removed in vacuo. The residue was dissolved in a small amount of water and then acidified (pH˜4) by the addition of 2N hydrogen chloride. The precipitate was collected and dried to afford 140 mg (quantitative) of 3-cyano-5-(1H-imidazol-1-yl-methyl)benzoic acid.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in a small amount of water
  3. additionby the addition of 2N hydrogen chloride
  4. customThe precipitate was collected
  5. customdried

Sources & evidence

ORD record
ord-74919ce4d8b144c69b502b502abbdb4e
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

Loading…