Sodium Hydroxide → HCID 86690740, compound

HRID 1471688Notes

Reaction equation

HRID 1471688 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[CH:5][C:4]=1[O:11][CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([CH:21]=1)[C:18]([O-:20])=[O:19])=[O:2].[OH-].[Na+]>CO.C1COCC1>[CH:1]([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[CH:5][C:4]=1[O:11][CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([CH:21]=1)[C:18]([OH:20])=[O:19])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86690741HCID 86690741, compound

Product 1

HCID 86690740HCID 86690740, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To 5-((4-formyl-6-methoxypyridin-3-yloxy)methyl)nicotinate (96 mg, 0.32 mmol, 1 eq.) in a mixture of MeOH/THF (1/3, 8.0 mL) was added NaOH (3 N, 1.7 mL, 5.1 mmol, 16 eq.). The mixture was stirred at rt for 2 h, acidified to pH 3, extracted with EtOAc (3×20 mL). The combined organic layers were dried over Na2SO4 and concentrated to give 5-((4-formyl-6-methoxypyridin-3-yloxy)methyl)nicotinic acid (86 mg, 93%) as a white solid. 1H NMR (400 MHz, DMSO) δ 13.55 (s, 1H), 10.34 (s, 1H), 9.06 (d, J=1.9 Hz, 1H), 8.96 (d, J=2.0 Hz, 1H), 8.42 (t, J=2.0 Hz, 1H), 8.34 (s, 1H), 7.02 (s, 1H), 5.44 (s, 2H), 3.86 (s, 3H). LRMS (M+H+) m/z 289.1.

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-715e857a1a3541d18ced82ed54b42622
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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