m-Chloroperbenzoic acid → HCID 68517369, compound

HRID 1948362Notes

Reaction equation

HRID 1948362 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])[CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:22])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])[N+:5]([O-:22])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59596919Isopropyl 4-Chloropicolinate2×

Product 1

HCID 68517369HCID 68517369, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.55 g (14 mmol) of isopropyl 4-chloropyridine-2-carboxylate (Intermediate 232) and 1.4 g (26 mmol) of m-CPBA in 30 ml CH2Cl2 was stirred at room temperature for 2 d. The mixture was quenched with aqueous NaHSO3 and CH2Cl2 was removed. The aqueous residue was basified with aqueous Na2CO3, saturated with NaCl and extracted repeatedly with EtOAc. The EtOAc was dried (MgSO4) and concentrated. The residue was taken up in ether and insoluble material was filtered off. The filtrate was concentrated and the residue was chromatographed on silica gel (100% CH2Cl2 with gradient elution to 100% EtOAc) to afford 2.1 g of product as an oil. NMR (d6-DMSO): 1.3 (d, 6H), 5.3 (septet, 1H), 7.25 (m, 1H), 7.5 (d, 1H), 8.1 (d, 1H).

Workup

  1. customThe mixture was quenched with aqueous NaHSO3 and CH2Cl2
  2. customwas removed
  3. extractionextracted repeatedly with EtOAc
  4. dry with materialThe EtOAc was dried (MgSO4)
  5. concentrationconcentrated
  6. filtrationinsoluble material was filtered off
  7. concentrationThe filtrate was concentrated
  8. customthe residue was chromatographed on silica gel (100% CH2Cl2 with gradient elution to 100% EtOAc)

Sources & evidence

ORD record
ord-bdbefc47e6474592bc9db04bf312e034
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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