Sodium Hydroxide → HCID 22047127, compound

HRID 1830535Notes

Reaction equation

HRID 1830535 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH:11]=[O:12])[CH:5]=[C:6]2[CH:10]=[CH:9][O:8][C:7]=12.[OH:13]P([O-])(O)=O.[K+].[O-]Cl=O.[Na+].[OH-].[Na+]>CS(C)=O.O>[Cl:1][C:2]1[N:3]=[C:4]([C:11]([OH:13])=[O:12])[CH:5]=[C:6]2[CH:10]=[CH:9][O:8][C:7]=12

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 516951Monobasic potassium phosphateHCID 10535409HCID 10535409, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 22047127HCID 22047127, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent3×

Procedure

C6 (3.0 g, 16.5 mmol) is dissolved in 40 mL DMSO. KH2PO4 (561 mg, 4.1 mmol) in 6.5 mL water is added and then NaClO2 (2.6 g, 23.1 mmol) in 24 mL water is added, and the reaction is stirred overnight at rt. The reaction is diluted with 200 mL water, the pH is adjusted to 9 with 2N NaOH, and any remaining aldehyde is extracted into 3×50 mL ether. The pH of the aqueous layer is adjusted to 3 with 10% aqueous HCl and is extracted with 4×50 mL EtOAc. The combined organic layer is dried over anhydrous MgSO4, filtered, and then concentrated in vacuo to a white solid. The solid is washed with ether and is dried to afford 7-chlorofuro[2,3-c]pyridine-5-carboxylic acid (C7) (55% yield). MS (CI) for C8H4ClNO3, m/z: 198 (M+H)+.

Workup

  1. extractionany remaining aldehyde is extracted into 3×50 mL ether
  2. extractionis extracted with 4×50 mL EtOAc
  3. dry with materialThe combined organic layer is dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a white solid
  6. washThe solid is washed with ether
  7. customis dried

Sources & evidence

ORD record
ord-3488b172d2df434c9cf8704b223bffc2
Source dataset
uspto-grants-2006_06
Patent number
US07067515B2

Reaction notes

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