Sodium Hydroxide → 5-Cyano-6-methoxy-4-methylpicolinic acid

HRID 1477028Notes

Reaction equation

HRID 1477028 reaction equation
[C:1]([C:3]1[C:4]([CH3:16])=[CH:5][C:6]([C:11]([O:13]CC)=[O:12])=[N:7][C:8]=1[O:9][CH3:10])#[N:2].[OH-].[Na+]>CO.C1COCC1>[C:1]([C:3]1[C:4]([CH3:16])=[CH:5][C:6]([C:11]([OH:13])=[O:12])=[N:7][C:8]=1[O:9][CH3:10])#[N:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67466404Ethyl 5-cyano-6-methoxy-4-methylpicolinate

Product 1

HCID 674675275-Cyano-6-methoxy-4-methylpicolinic acidYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of ethyl 5-cyano-6-methoxy-4-methylpicolinate (1.0 g, 4.54 mmol) in MeOH (30 mL) and THF (10 mL) was added 6N NaOH (2 mL, 12.00 mmol). The suspension was heated to 60° C. and stirred for 2 hr. (The reaction cleared up right away.) LCMS indicated that the reaction was complete. The reaction was cooled to RT and concentrated to near dryness. The slurry was neutralized with 6N HCl (2 mL) diluted with water, filtered, washed with water and dried under vacuum to give the product 5-cyano-6-methoxy-4-methylpicolinic acid (0.76 g, 3.95 mmol, 87% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 13.65 (br. s., 1H), 7.73 (s, 1H), 4.03 (s, 3H), 2.54 (s, 3H). MS(ES)+m/e 192.9 [M+H]+.

Workup

  1. temperatureThe reaction was cooled to RT
  2. concentrationconcentrated
  3. additiondiluted with water
  4. filtrationfiltered
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-4fdb285dc6c542ee9bafc92a6cc42915
Source dataset
uspto-grants-2016_08
Patent number
US09402836B2

Reaction notes

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