Sulfamic Acid → 5-Fluoro-2-methoxynicotinic acid

HRID 509998Notes

Reaction equation

HRID 509998 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[O:11])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.Cl([O-])=[O:13].[Na+].O1CCOCC1.S(=O)(=O)(O)N>O>[F:1][C:2]1[CH:7]=[N:6][C:5]([O:8][CH3:9])=[C:4]([CH:3]=1)[C:10]([OH:13])=[O:11]

Participants

6

Reactant 4

HCID 5987Sulfamic AcidHCID 312751,4-DioxaneHCID 226783235-Fluoro-2-methoxynicotinaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 404270085-Fluoro-2-methoxynicotinic acidYield 92.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

In a round bottom flask, 5-fluoro-2-methoxy-pyridine-3-carbaldehyde (37, 0.500 g, 3.22 mmol) was combined with sodium chlorite (0.6734 g, 5.957 mmol), 30 mL of 1,4-dioxane, 10 mL of water, and sulfamic acid (2.39 g, 24.6 mmol). The reaction mixture was stirred at room temperature for 5 minutes, then poured into 100 mL of water and extracted with 100 mL of ethyl acetate. The organic layer was washed with water, brine, then dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum to provide the desired compound (150, 512 mg), used in the next step without further purification.

Workup

  1. extractionextracted with 100 mL of ethyl acetate
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-bbee6f56fd694b78920c04558da802e4
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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