Sodium Hydroxide → 2-[N-(2-(2-thienylmethoxy)-5-bromobenzyl)-N-ethylamino]pyridine-5-carboxylic acid

HRID 1455965Notes

Reaction equation

HRID 1455965 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][O:7][C:8]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:9]=1[CH2:10][N:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]([O:22]C)=[O:21])=[CH:16][N:15]=1)[CH2:12][CH3:13].[OH-].[Na+]>CO>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][O:7][C:8]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:9]=1[CH2:10][N:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][N:15]=1)[CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22105529methyl 2-[N-(2-(2-thienylmethoxy)-5-bromobenzyl)-N-ethylamino]pyridine-5-carboxylate

Product 1

HCID 221056602-[N-(2-(2-thienylmethoxy)-5-bromobenzyl)-N-ethylamino]pyridine-5-carboxylic acidYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 2-[N-(2-(2-thienylmethoxy)-5-bromobenzyl)-N-ethylamino]pyridine-5-carboxylate (0.53 g, 1.15 mmol) in methanol (25 mL) was treated with aqueous sodium hydroxide (2N, 5 mL). The reaction was heated to reflux for 9 hours. The reaction mixture was cooled and evaporated and residue was diluted with water and acidified with acetic acid. The off-white solid was filtered off to give 2-[N-(2-(2-thienylmethoxy)-5-bromobenzyl)-N-ethylamino]pyridine-5-carboxylic acid (0.41 g, 91%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 9 hours
  3. temperatureThe reaction mixture was cooled
  4. customevaporated
  5. additionresidue was diluted with water
  6. filtrationThe off-white solid was filtered off

Sources & evidence

ORD record
ord-bdf0f30b41cf4f889a7a8fc634ccd51e
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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