Chlorosuccinimide → 3-Chloro-4-(2,4-difluorobenzyloxy)-1H-pyridin-2-one

HRID 1866901Notes

Reaction equation

HRID 1866901 reaction equation
[F:1][C:2]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[CH:10][NH:9][C:8](=[O:12])[CH:7]=1.[Cl:18]N1C(=O)CCC1=O>CC(O)=O>[Cl:18][C:7]1[C:8](=[O:12])[NH:9][CH:10]=[CH:11][C:6]=1[O:5][CH2:4][C:3]1[CH:13]=[CH:14][C:15]([F:17])=[CH:16][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 220503904-(2,4-difluorobenzyloxy)-1H-pyridin-2-one

Product 1

HCID 220499783-Chloro-4-(2,4-difluorobenzyloxy)-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-[(4-fluorobenzyl)oxy]pyridine-2(1H)-one (from Step 2, Example 74) (1.4 g, 5.9 mmol) in AcOH (25 mL) was added N-chlorosuccinimide (0.95 g, 7.1 mmol) and the reaction mixture was heated at reflux for 2 h. The solvent was removed under reduced pressure. 1H NMR (300 MHz, MeOD) δ 7.63-7.55 (m, 1H), 7.45 (d, J=8 Hz, 1H), 7.07-7.00 (m, 2H), 6.58 (d, J=8 Hz, 1H), 5.31 (d, J=8 Hz, 1H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-dd8f981d13cf435d9107c08f3dd4be53
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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