Water → 5-(Benzyloxy)pyridine-2-carboxylic acid

HRID 1950009Notes

Reaction equation

HRID 1950009 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[O:16])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.S(=O)(=O)([OH:20])N.Cl([O-])=O.[Na+]>CC(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([OH:20])=[O:16])=[N:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5987Sulfamic AcidHCID 123972545-(Benzyloxy)pyridine-2-carbaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 183793525-(Benzyloxy)pyridine-2-carboxylic acidYield 73.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-benzyloxypyridine-2-carbaldehyde (3.8 g) in acetone (50 ml) was added water (50 ml), sulfamic acid (2.4 g) and sodium chlorite (2.2 g) were sequentially added thereto on an ice bath, and the solution was stirred for 6 hours at room temperature. The solid that was precipitated was filtered and rinsed with water to provide the title compound (3.0 g).

Workup

  1. additionwere sequentially added
  2. customThe solid that was precipitated
  3. filtrationwas filtered
  4. washrinsed with water

Sources & evidence

ORD record
ord-89d035fca62745bca76173e20e6a7228
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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