2,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehyde → 2,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carboxylic acid

HRID 1509850Notes

Reaction equation

HRID 1509850 reaction equation
[O:1]1[C:10]2[CH:9]=[C:8]([CH:11]=[O:12])[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1.Cl([O-])=[O:14].[Na+].P([O-])(O)(O)=O.[Na+]>CC(O)(C)C.CC(=CC)C.O>[O:1]1[C:10]2[CH:9]=[C:8]([C:11]([OH:14])=[O:12])[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 218736682,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehydeHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 218736242,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carboxylic acidYield 51.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 105532-Methyl-2-buteneSolvent

Procedure

To a solution of 2,3-dihydro-[1,4]dioxino[2,3-c]pyridine-7-carbaldehyde (722 mg, 4.37 mmol) in 2-methyl-2-propanol (95 mL) and 2-methyl-2-butene (22 mL) was added dropwise a solution of sodium chlorite (80%, 4.55 g, 40.22 mmol) and sodium dihydrogenphosphate (3.65 g, 26.45 mmol) in water (35 mL). The resulting solution was stirred at rt for 19 h. The volatiles were removed under reduced pressure. The residue was diluted with water (20 mL) and pH was adjusted to 3 by addition of 1N HCl. The aq. layer was extracted with DCM-MeOH 9-1 (25×30 mL). The combined extracts were dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was triturated in ether and filtered to give the title acid as a white solid (0.405 g, 51% yield).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. additionThe residue was diluted with water (20 mL) and pH
  3. additionwas adjusted to 3 by addition of 1N HCl
  4. extractionThe aq. layer was extracted with DCM-MeOH 9-1 (25×30 mL)
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was triturated in ether
  9. filtrationfiltered

Sources & evidence

ORD record
ord-2829e531b0f64600bf5277c9951c20fb
Source dataset
uspto-grants-2012_07
Patent number
US08211890B2

Reaction notes

Loading…