Peracetic Acid → Methyl 5-chloro-2-(3-fluorophenyl)nicotinate 1-oxide

HRID 717815Notes

Reaction equation

HRID 717815 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(OO)(=[O:21])C>>[Cl:1][C:2]1[CH:3]=[N+:4]([O-:21])[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

3

Reactant 2

HCID 6585Peracetic AcidHCID 58515983Methyl 5-chloro-2-(3-fluorophenyl)nicotinate

Product 1

HCID 66993068Methyl 5-chloro-2-(3-fluorophenyl)nicotinate 1-oxideYield 68%

Procedure

A solution of methyl 5-chloro-2-(3-fluorophenyl)nicotinate (11 g, 41 mmol) in ethaneperoxoic acid (30 mL, 100 mmol) was heated at 90° C. for 1 hour. Evaporation and purification by flash column chromatography with ethyl acetate in hexanes (0-50%) gave the desired compound (7.0 g, 68%). LCMS calculated for C13H10ClFNO3 (M+H)+: m/z=282.0. found: 281.8. 1H NMR (300 MHz, DMSO-d6): δ 8.83 (s, 1H), 7.85 (s, 1H), 7.49 (m, 1H), 7.25 (m, 2H), 7.14 (m, 1H), 3.32 (s, 3H).

Workup

  1. customEvaporation and purification by flash column chromatography with ethyl acetate in hexanes (0-50%)

Sources & evidence

ORD record
ord-16567f5162884ae68ef70c9b09688fde
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

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