Methanol → 3,5-Bis(benzyloxy)picolinic acid

HRID 1908286Notes

Reaction equation

HRID 1908286 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:23]#N)=[N:11][CH:12]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:25].[Na+].C[OH:28]>>[CH2:1]([O:8][C:9]1[C:10]([C:23]([OH:28])=[O:25])=[N:11][CH:12]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 534879943,5-Bis(benzyloxy)picolinonitrile

Product 1

HCID 534879953,5-Bis(benzyloxy)picolinic acid

Procedure

To a solution of 3,5-bis-benzyloxy-pyridine-2-carbonitrile, 1, (26.0 g, 82.3 mmol) in MeOH (217 mL) is added 30% w/v sodium hydroxide (320 mL) and the reaction mixture is refluxed for 16 hours. The solvent is removed under reduced pressure and the resulting suspension is acidified with conc. HCl until the pH is between 1 and 2. The precipitate that results is collected by filtration, washed with H2O (10 mL) and dried overnight in a vacuum oven to afford 30 g (quantitative) of the desired product as the hydrochloride salt. 1H NMR (250 MHz, DMSO-d6) δ ppm 8.02 (1H, d, J=2.4 Hz), 7.29-7.53 (11H, m), 5.96 (1H, br s), 5.28 (4H, s). HPLC-MS: m/z 336 [M+H]+.

Workup

  1. temperaturethe reaction mixture is refluxed for 16 hours
  2. customThe solvent is removed under reduced pressure
  3. customThe precipitate that results
  4. filtrationis collected by filtration
  5. washwashed with H2O (10 mL)
  6. customdried overnight in a vacuum oven

Sources & evidence

ORD record
ord-a351d06247b441e6bdee97ca134277c7
Source dataset
uspto-grants-2013_12
Patent number
US08598210B2

Reaction notes

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