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

HRID 1616858Notes

Reaction equation

HRID 1616858 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 6 N NaOH (2 mL, 12.00 mmol). The suspension was heated to 60° C. and stirred for 2 h. (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 6 N 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-93a2db9e92354298882b0ce0a1873d7a
Source dataset
uspto-grants-2014_07
Patent number
US08765792B2

Reaction notes

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