Hydrochloric Acid → 5-Hydroxy-2-methoxyisonicotinaldehyde

HRID 1471709Notes

Reaction equation

HRID 1471709 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, 1 eq.) in THF (150 mL) was added HCl (3 N, 250 mL, 4.4 eq.). 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 to give 5-hydroxy-2-methoxyisonicotinaldehyde (17.9 g, 74.6%) as a pale yellow solid. 1H NMR (400 MHz; DMSO) δ=10.31 (s, 1H), 8.03 (s, 1H), 6.89 (s, 1H), 3.80 (s, 3H). LRMS (M+H+) m/z 154.0.

Workup

  1. temperaturecooled to rt
  2. customThe pale yellow solid was collected
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-38f5001b59a245dc80b8e7df135cf703
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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