Sodium Hydroxide → HCID 22047327, compound

HRID 1830566Notes

Reaction equation

HRID 1830566 reaction equation
[CH:1]1[C:6]2[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[O:9][C:5]=2[CH:4]=[C:3]([C:14]([O:16]C)=[O:15])[N:2]=1.[OH-].[Na+]>CO.O>[CH:1]1[C:6]2[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[O:9][C:5]=2[CH:4]=[C:3]([C:14]([OH:16])=[O:15])[N:2]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22047181HCID 22047181, compound

Product 1

HCID 22047327HCID 22047327, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl benzofuro[3,2-c]pyridine-3-carboxylate (2.02 g, 8.89 mmol) is dissolved in MeOH (50 ml) and water (10 ml). 2M NaOH (5.3 ml, 10.67 mmol) is added dropwise, and the reaction stirred overnight at rt. When the reaction is complete by TLC, the volatiles are removed in vacuo. The solid residue is suspended in water (40 ml) and the pH is adjusted to 3 with concentrated HCl. The white slurry is filtered, and the cake is dried first in a stream of air and then in a vacuum oven overnight, affording 1.84 g (97%) of benzofuro[3,2-c]pyridine-3-carboxylic acid as a pale yellow solid. 1H NMR (DMSO-d6) δ 7.56 (t, J=8 Hz), 7.68 (t, J=7 Hz), 7.877 (d, J=8 Hz), 8.38 (m), 9.51 ppm.

Workup

  1. customthe volatiles are removed in vacuo
  2. filtrationThe white slurry is filtered
  3. customthe cake is dried first in a stream of air

Sources & evidence

ORD record
ord-40b4e081bbb94fef901ea3c0c5fd2119
Source dataset
uspto-grants-2006_06
Patent number
US07067515B2

Reaction notes

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