Hydrochloric Acid → 5-chloro-1-(4-fluorophenyl)-3-methoxypyrazin-2(1H)-one

HRID 2241370Notes

Reaction equation

HRID 2241370 reaction equation
Cl[C:2]1[C:3](=[O:16])[N:4]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[CH:5]=[C:6]([Cl:8])[N:7]=1.[CH3:17][O-:18].[Na+].Cl>CO>[Cl:8][C:6]1[N:7]=[C:2]([O:18][CH3:17])[C:3](=[O:16])[N:4]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 672211573,5-dichloro-1-(4-fluorophenyl)pyrazin-2(1H)-one

Product 1

HCID 673472395-chloro-1-(4-fluorophenyl)-3-methoxypyrazin-2(1H)-oneYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3,5-dichloro-1-(4-fluorophenyl)pyrazin-2(1H)-one (13.0 g, 50.2 mmol; prepared by according to the general methods described by M. Tutonda, et al., Tetrahedron, 1990, 46, 5715) dissolved in absolute methanol (100 mL) was treated with NaOMe (6.78 g, 125 mmol). The reaction mixture was stirred at room temperature for 1 hour, neutralized with 2 N HCl (Et2O solution), and evaporated the solvent under reduced pressure. The residue was treated with EtOAc, washed with 0.5 N HCl, dried over MgSO4, and concentrated under reduced pressure to give the desired product (12.8 g, 100%). LRMS (ESI pos) m/e 254.9, 256.9 (M+1, Cl pattern).

Workup

  1. customprepared
  2. customevaporated the solvent under reduced pressure
  3. additionThe residue was treated with EtOAc
  4. washwashed with 0.5 N HCl
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5e73a246faa346aa8b93c473036c357f
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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