Phosphorus oxychloride → 7-chlorofuro[2,3-c]pyridin-3(2H)-one O-methyl oxime

HRID 1508213Notes

Reaction equation

HRID 1508213 reaction equation
[CH3:1][O:2][N:3]=[C:4]1[C:12]2[C:7](=[CH:8][N+:9]([O-])=[CH:10][CH:11]=2)[O:6][CH2:5]1.P(Cl)(Cl)([Cl:16])=O>C(Cl)Cl>[CH3:1][O:2][N:3]=[C:4]1[C:12]2[C:7](=[C:8]([Cl:16])[N:9]=[CH:10][CH:11]=2)[O:6][CH2:5]1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 867219123-(Methoxyimino)-2,3-dihydrofuro[2,3-c]pyridine 6-oxide

Product 1

HCID 867219137-chlorofuro[2,3-c]pyridin-3(2H)-one O-methyl oxime

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-(methoxyimino)-2,3-dihydrofuro[2,3-c]pyridine 6-oxide (5.35 mmol) in 30 mL DCM were added 2.9 mL phosphoryl chloride at 0° C. The mixture was heated to 50° C. for 7 h, concentrated in vacuo, redissolved in DCM and quenched with solid NaHCO3 and then water. The aqueous layer was extracted with DCM (2×). The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification by CC (KP-SIL™ from Biotage) using Hept/EtOAc (8/2) gives the desired product as beige solid;

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionredissolved in DCM
  3. customquenched with solid NaHCO3
  4. extractionThe aqueous layer was extracted with DCM (2×)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification by CC (KP-SIL™ from Biotage)

Sources & evidence

ORD record
ord-a35acd468d164dcaa1c412bf5624a134
Source dataset
uspto-grants-2015_12
Patent number
US09221832B2

Reaction notes

Loading…