Sodium Hydroxide → 5-(2,2,2-Trifluoroethoxy)pyridine-2-carboxylic acid

HRID 341532Notes

Reaction equation

HRID 341532 reaction equation
[F:1][C:2]([F:16])([F:15])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([O:13]C)=[O:12])=[N:9][CH:10]=1.[OH-].[Na+]>CO>[F:16][C:2]([F:1])([F:15])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])=[O:12])=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57475873Methyl 5-(2,2,2-trifluoroethoxy)pyridine-2-carboxylate2×

Product 1

HCID 574758545-(2,2,2-Trifluoroethoxy)pyridine-2-carboxylic acidYield 29%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 5-(2,2,2-trifluoroethoxy)pyridine-2-carboxylate (Intermediate 223, 0.650 g, 2.77 mmol) was dissolved in MeOH (10 mL), 2M aq. sodium hydroxide (3.46 mL, 6.93 mmol) was added and the mixture stirred at room temperature for 2 h. MeOH was removed under vacuum and the aqueous suspension neutralised by adding 2M aq. hydrochloric acid (3.5 mL). The resultant precipitate was filtered, washed with diethyl ether and dried under vacuum to afford the title compound as a white solid (0.179 mg, 29%). 1H NMR (500 MHZ, MeOH-d4) δ ppm 8.41 (1H, d), 8.15 (1H, d), 7.59 (1H, dd) and 4.77 (2H, q).

Workup

  1. customMeOH was removed under vacuum
  2. additionby adding 2M aq. hydrochloric acid (3.5 mL)
  3. filtrationThe resultant precipitate was filtered
  4. washwashed with diethyl ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-86429120c9c94636bb7df0321a094fd9
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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