Chlorosuccinimide → 3-chloro-1-(2,6-difluorophenyl)-4-hydroxy-6-methylpyridin-2(1H)-one

HRID 1867030Notes

Reaction equation

HRID 1867030 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]([CH3:15])=[CH:13][C:12]([OH:16])=[CH:11][C:10]1=[O:17].C1C(=O)N([Cl:25])C(=O)C1>ClCCl>[Cl:25][C:11]1[C:10](=[O:17])[N:9]([C:3]2[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[C:14]([CH3:15])=[CH:13][C:12]=1[OH:16]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 54724198HCID 54724198, compound

Product 1

HCID 547242093-chloro-1-(2,6-difluorophenyl)-4-hydroxy-6-methylpyridin-2(1H)-oneYield 79.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-(2,6-difluorophenyl)-4-hydroxy-6-methylpyridin-2(1H)-one (0.30 g, 1.26 mmol) in dichloromethane (5 mL) was added NCS (2.52 g, 1.90 mmol). The reaction mixture stirred at room temperature under nitrogen for 4.5 hours. The suspension was cooled in ice bath, filtered, and the solid was rinsed with fresh dichloromethane to afford the desired product (0.271 g, 79%) as a white solid. 1H-NMR (CD3OD, 400 MHz) δ 7.58 (m, 1H), 7.22 (m, 2H), 6.20 (s 1H), 2.00 (s, 3H); ES-HRMS m/z 272.0287 (M+H calculated for C12H9NO2F2Cl requires 272.0290).

Workup

  1. temperatureThe suspension was cooled in ice bath
  2. filtrationfiltered
  3. washthe solid was rinsed with fresh dichloromethane

Sources & evidence

ORD record
ord-6b53308172274e27abbf6940dbae7f4a
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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