Sodium Hydroxide → 6-(2-(2,2,2-Trifluoroethoxy)ethoxy)nicotinic acid

HRID 341545Notes

Reaction equation

HRID 341545 reaction equation
[F:1][C:2]([F:19])([F:18])[CH2:3][O:4][CH2:5][CH2:6][O:7][C:8]1[N:13]=[CH:12][C:11]([C:14]([O:16]C)=[O:15])=[CH:10][CH:9]=1.[OH-].[Na+]>CO>[F:19][C:2]([F:1])([F:18])[CH2:3][O:4][CH2:5][CH2:6][O:7][C:8]1[N:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66803048Methyl 6-[2-(2,2,2-trifluoroethoxy)ethoxy]pyridine-3-carboxylate2×

Product 1

HCID 593549156-(2-(2,2,2-Trifluoroethoxy)ethoxy)nicotinic acidYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 6-[2-(2,2,2-trifluoroethoxy)ethoxy]pyridine-3-carboxylate (Intermediate 243, 0.453 g, 1.62 mmol) was dissolved in MeOH (5 mL), 2M aq. sodium hydroxide (1.62 mL, 3.24 mmol) was added and the mixture was stirred at room temperature for 1 h. The mixture was then concentrated under vacuum and acidified with 2M hydrochloric acid. The resultant precipitate was filtered off and dried under vacuum to afford the title compound as a white solid (0.245 g, 57%). 1H NMR (500 MHZ, MeOH-d4) δ ppm 8.79 (1H, d), 8.23 (1H, dd), 6.90 (1H, d), 4.55 (2H, dd), 4.03 (2H, q) and 4.01 (2H, dd).

Workup

  1. concentrationThe mixture was then concentrated under vacuum
  2. filtrationThe resultant precipitate was filtered off
  3. customdried under vacuum

Sources & evidence

ORD record
ord-a48c2acc145247a0acfd9de77faf8318
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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