Methyl 6-thien-2-ylnicotinate → 6-(Thiophen-2-Yl)Pyridine-3-Carboxylic Acid

HRID 440766

Reaction equation

HRID 440766 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:11]=[CH:10][C:9]([C:12]([O:14]C)=[O:13])=[CH:8][CH:7]=1>CO.[OH-].[Na+]>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:11]=[CH:10][C:9]([C:12]([OH:14])=[O:13])=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 17879034Methyl 6-thien-2-ylnicotinate

Product 1

HCID 154111446-(Thiophen-2-Yl)Pyridine-3-Carboxylic Acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2.0 g of methyl 6-(2-thienyl)pyridine-3-carboxylate in 100 ml of methyl alcohol and 50 ml of 5N sodium hydroxide is stirred at room temperature for 16 hours under nitrogen. The reaction mixture is evaporated in vacuo to about one quarter of the volume and then diluted with 150 ml of cold water. The pH is adjusted to 4 with acetic acid and the desired white product collected, washed with 400 ml of cold water until neutral. The solid is washed with 50 ml of petroleum ether and dried under vacuum to 40° C. to give the desired product.

Workup

  1. customThe reaction mixture is evaporated in vacuo to about one quarter of the volume
  2. additiondiluted with 150 ml of cold water
  3. customthe desired white product collected
  4. washwashed with 400 ml of cold water until neutral
  5. washThe solid is washed with 50 ml of petroleum ether
  6. customdried under vacuum to 40° C.

Sources & evidence

ORD record
ord-99a7d22472914ee8a67a8d1bd0cba47d
Source dataset
uspto-grants-1996_05
Patent number
US05521173

Linked notes

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