Sodium Hydroxide → 5-Cyano-6-ethoxynicotinic acid

HRID 1820972Notes

Reaction equation

HRID 1820972 reaction equation
[C:1]([C:3]1[C:4]([O:13][CH:14](C)[C:15](F)(F)F)=[N:5][CH:6]=[C:7]([CH:12]=1)[C:8]([O:10]C)=[O:9])#[N:2].[OH-].[Na+]>CCO>[C:1]([C:3]1[C:4]([O:13][CH2:14][CH3:15])=[N:5][CH:6]=[C:7]([CH:12]=1)[C:8]([OH:10])=[O:9])#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68850684Methyl 5-cyano-6-(2,2,2-trifluoro-1-methylethoxy)nicotinate

Product 1

HCID 575059565-Cyano-6-ethoxynicotinic acidYield 45.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 498 mg (1.82 mmol) of methyl 5-cyano-6-(2,2,2-trifluoro-1-methylethoxy)nicotinate (from CARBOXYLIC ACID 20, Step C) in 10 mL of EtOH was added 1.8 mL of 5.0 N NaOH. After stirring at rt overnight, the mixture was acidified using Dowex H cation exchange resin until pH=3. The resin was filtered off and the filtrate was concentrated to give 160 mg of the title compound: 1H NMR (500 MHz, CD3OD) δ 1.37 (t, J=7.1, 3H), 4.50 (d, J=7.1, 2H), 8.43 (d, J=2.1, 1H), 8.85 (d, J=2.3, 1H).

Workup

  1. filtrationThe resin was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-eed1bb8ee32142429d523ce30c5f7d80
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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