Hydrochloric Acid → 5-Hydroxy-2-methoxyisonicotinaldehyde

HRID 1471682Notes

Reaction equation

HRID 1471682 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:8]([O:11]COC)=[CH:9][N:10]=1)[CH:6]=[O:7].Cl>C1COCC1.O>[OH:11][C:8]1[C:5]([CH:6]=[O:7])=[CH:4][C:3]([O:2][CH3:1])=[N:10][CH:9]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 121807202-Methoxy-5-(methoxymethoxy)-4-pyridinecarboxaldehyde

Product 1

HCID 722124985-Hydroxy-2-methoxyisonicotinaldehydeYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-methoxy-5-(methoxymethoxy)isonicotinaldehyde (10 g, 0.05 mol) in THF (100 mL) was added 3 N HCl (150 mL). The reaction was stirred at 50° C. for 30 min, cooled to rt, and diluted with water (100 mL). The mixture was neutralized to pH 7-8 and extracted with EtOAc (200 mL) three times. The organic layer was dried over Na2SO4 and concentrated to give 5-hydroxy-2-methoxyisonicotinaldehyde (4.2 g, 55%) as a yellow solid. 1H NMR (400 MHz; DMSO) δ=10.31 (s, 1H), 8.03 (s, 1H), 6.89 (s, 1H), 3.80 (s, 3H).

Workup

  1. temperaturecooled to rt
  2. extractionextracted with EtOAc (200 mL) three times
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-88edf30cdd7748b6ad5c64e85f675faa
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

Loading…