Lithium Hydroxide → 3-(6-Chloropyridin-3-yl)prop-2-enoic acid

HRID 2265931Notes

Reaction equation

HRID 2265931 reaction equation
C[O:2][C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:7]=[N:8][C:9]([Cl:12])=[CH:10][CH:11]=1.[Li+].[OH-]>C1COCC1.O>[Cl:12][C:9]1[N:8]=[CH:7][C:6]([CH:5]=[CH:4][C:3]([OH:13])=[O:2])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 719484463-(6-Chloro-pyridin-3-yl)-acrylic acid methyl ester

Product 1

HCID 534250563-(6-Chloropyridin-3-yl)prop-2-enoic acidYield 80.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-(6-Chloro-pyridin-3-yl)-acrylic acid methyl ester (107 mg, 0.541 mmol) in THF was added to a solution of 0.5 N-LiOH (2 eq) and the mixture was stirred for 3 hrs at room temperature. The resulting residue was dissolved in H2O and then washed three times with Et2O, neutralized with 1N HCl to pH 5˜7. The resulting solid filtered and washed with H2O and then dried in vacuo to give 3-(6-chloro-pyridin-3-yl)-acrylic acid (80 mg, 80%).

Workup

  1. washwashed three times with Et2O
  2. filtrationThe resulting solid filtered
  3. washwashed with H2O
  4. customdried in vacuo

Sources & evidence

ORD record
ord-c84e9f57576742bf87ee4b47bc09fd28
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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