Hydrochloric Acid → 5-Hydroxy-2-methoxyisonicotinaldehyde

HRID 1847950Notes

Reaction equation

HRID 1847950 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.C([O-])([O-])=O.[K+].[K+]>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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 121807202-Methoxy-5-(methoxymethoxy)-4-pyridinecarboxaldehyde

Product 1

HCID 722124985-Hydroxy-2-methoxyisonicotinaldehydeYield 74.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-methoxy-5-(methoxymethoxy)isonicotinaldehyde (33.5 g, 0.17 mol) in THF (150 mL) was added HCl (3 N, 250 mL). The reaction was stirred at 50° C. for 1 h, cooled to RT and diluted with water (500 mL). The mixture was neutralized to pH 7-8 with solid K2CO3. The pale yellow solid was collected, washed with water, and dried in vacuum oven (40° C.) overnight to give 5-hydroxy-2-methoxyisonicotinaldehyde (17.9 g, 74.6%). 1H NMR (400 MHz; DMSO)=10.31 (s, 1H), 8.03 (s, 1H), 6.89 (s, 1H), 3.80 (s, 3H); MS (ESI) m/z 154.0 [M+H]+.

Workup

  1. temperaturecooled to RT
  2. customThe pale yellow solid was collected
  3. washwashed with water
  4. customdried in vacuum oven (40° C.) overnight

Sources & evidence

ORD record
ord-fdf63c97dbd84de5bc09a69a99fe6e73
Source dataset
uspto-grants-2015_02
Patent number
US08952171B2

Reaction notes

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