Monobasic potassium phosphate → 3-Chlorofuro[2,3-c]pyridine-5-carboxylic acid

HRID 1830553Notes

Reaction equation

HRID 1830553 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[C:8]([CH:11]=[O:12])[CH:9]=2)[O:4][CH:3]=1.Cl([O-])=[O:14].[Na+].OP([O-])(O)=O.[K+]>C1COCC1.CC(O)(C)C.O>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[C:8]([C:11]([OH:14])=[O:12])[CH:9]=2)[O:4][CH:3]=1

Participants

7

Reactant 3

HCID 516951Monobasic potassium phosphateHCID 22047393HCID 22047393, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 220474433-Chlorofuro[2,3-c]pyridine-5-carboxylic acidYield 105.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Chlorofuro[2,3-c]pyridine-5-carbaldehyde (317 mg, 1.74 mmol) is dissolved in THF (10 mL)/t-BuOH (5 mL)/H2O (5 mL), treated with a single portion of sodium chlorite (592 mg, 5.24 mmol) and KH2PO4 (473 mg, 3.48 mmol) and stirred at rt for 18 h. The reaction mixture is concentrated in vacuo to dryness, suspended in water (10 μL), acidified to pH 3.5 with concentrated HCl and stirred at rt for 2 h. The resulting solid is filtered, washed with water and dried in a vacuum oven at 40° C. for 18 h to afford 364 mg of 3-chlorofuro[2,3-c]pyridine-5-carboxylic acid as a white solid. MS (EI) m/z: 197 (M+).

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo to dryness
  2. stirringstirred at rt for 2 h
  3. filtrationThe resulting solid is filtered
  4. washwashed with water
  5. customdried in a vacuum oven at 40° C. for 18 h

Sources & evidence

ORD record
ord-12d8061472c54c35956b76274198c5af
Source dataset
uspto-grants-2006_06
Patent number
US07067515B2

Reaction notes

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