Methanol → 3-(4-Methoxybenzylamino)-6-methyl-1-carboxymethyl pyrazinone

HRID 322546Notes

Reaction equation

HRID 322546 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][NH:8][C:9]2[C:10](=[O:21])[N:11]([CH2:17][C:18]([OH:20])=[O:19])[C:12]([CH3:16])=[C:13](Cl)[N:14]=2)=[CH:5][CH:4]=1.CO>[OH-].[Na+].[Ni]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9]2[C:10](=[O:21])[N:11]([CH2:17][C:18]([OH:20])=[O:19])[C:12]([CH3:16])=[CH:13][N:14]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 220087753-(4-Methoxybenzylamino)-5-chloro-6-methyl-1-carboxymethylpyrazinone

Product 1

HCID 220087443-(4-Methoxybenzylamino)-6-methyl-1-carboxymethyl pyrazinone

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 14798Sodium HydroxideSolvent2×

Procedure

The acid 18-5 (810 mg) was dissolved in 40 mL 1 N NaOH and 40 mL MeOH at room temperature and was treated with Raney nickel suspension (˜5 g). A second charge of Raney nickel (˜5 g) and 1 N NaOH (20 mL) was added after 3 h. After 6 h, the suspension was filtered through celite washing with water and MeOH. The volatiles were removed in vacuo and the residue then taken up 1 N HCl (˜5 mL). Saturated NaHCO3 solution was added until pH˜7-8 and the solution was extracted exhaustively with EtOAc/THF. After drying (MgSO4), the solvent was removed to give the title compound 18-6 as a solid which was used as such:

Workup

  1. additionwas added after 3 h
  2. filtrationthe suspension was filtered
  3. washthrough celite washing with water and MeOH
  4. customThe volatiles were removed in vacuo
  5. additionSaturated NaHCO3 solution was added until pH˜7-8
  6. extractionthe solution was extracted exhaustively with EtOAc/THF
  7. dry with materialAfter drying (MgSO4)
  8. customthe solvent was removed

Sources & evidence

ORD record
ord-aa6565d917c94eeeb5adde5209ebf99d
Source dataset
uspto-grants-2001_04
Patent number
US06211184B1

Reaction notes

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