Sulfamic Acid → 6-(Difluoromethoxy)[1]benzofuro[3,2-c]pyridine-9-carboxylic acid

HRID 39331

Reaction equation

HRID 39331 reaction equation
[F:1][CH:2]([F:19])[O:3][C:4]1[C:9]2[O:10][C:11]3[CH:16]=[CH:15][N:14]=[CH:13][C:12]=3[C:8]=2[C:7]([CH:17]=[O:18])=[CH:6][CH:5]=1.S(=O)(=O)([OH:22])N.Cl([O-])=O.[Na+]>CC(C)=O.O>[F:19][CH:2]([F:1])[O:3][C:4]1[C:9]2[O:10][C:11]3[CH:16]=[CH:15][N:14]=[CH:13][C:12]=3[C:8]=2[C:7]([C:17]([OH:22])=[O:18])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 23668197Sodium ChloriteHCID 593961516-(Difluoromethoxy)[1]benzofuro[3,2-c]pyridine-9-carbaldehyde

Product 1

HCID 593961556-(Difluoromethoxy)[1]benzofuro[3,2-c]pyridine-9-carboxylic acidYield 97%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a well stirred solution of 6-(difluoromethoxy)[1]benzofuro[3,2-c]pyridine-9-carbaldehyde (500 mg, 1.90 mmol) in acetone (10 mL) was added sulphamic acid (276 mg, 2.85 mmol) at about 10° C. followed by drop wise addition of a solution of sodium chlorite (240 mg, 2.66 mmol) in water (5 mL) at about 0 to 5° C. The mixture was then stirred for about 1-2 hours. Ice cold water (50 mL) was added and the mixture was stirred for about 30 hours. The solid which separated was filtered, washed with water (3×5 mL) and dried at about 60-70° C. to give 6-(difluoromethoxy)[1]benzofuro[3,2-c]pyridine-9-carboxylic acid as a white solid.

Workup

  1. stirringthe mixture was stirred for about 30 hours
  2. customThe solid which separated
  3. filtrationwas filtered
  4. washwashed with water (3×5 mL)
  5. customdried at about 60-70° C.

Sources & evidence

ORD record
ord-0bbc3258de874f4a95fa95d492a7d15b
Source dataset
uspto-grants-2013_09
Patent number
US08524905B2

Linked notes

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