Sodium Hydroxide → HCID 22047127, compound

HRID 1072986Notes

Reaction equation

HRID 1072986 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 H2O is added and then NaClO2 (2.6 g, 23.1 mmol) in 24 mL H2O is added, and the reaction is stirred overnight at rt. The reaction is diluted with 200 mL H2O, 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 MgSO4, filtered, and concentrated in vacuo to a white solid. The solid is washed with ether and 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 MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a white solid
  6. washThe solid is washed with ether
  7. customdried

Sources & evidence

ORD record
ord-6e006a9dc5f9483fad965618d31818c0
Source dataset
uspto-grants-2005_06
Patent number
US06911543B2

Reaction notes

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