Sodium Bicarbonate → 1-(4-Methoxybenzyl)-5-bromo-4-methyl-3-amino-2-pyridone

HRID 1005404Notes

Reaction equation

HRID 1005404 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[CH:13]=[C:12]([Br:14])[C:11]([CH3:15])=[C:10]([N+:16]([O-])=O)[C:9]2=[O:19])=[CH:5][CH:4]=1.C([O-])(O)=O.[Na+]>C(O)(=O)C.Cl.O>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[CH:13]=[C:12]([Br:14])[C:11]([CH3:15])=[C:10]([NH2:16])[C:9]2=[O:19])=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 217064791-(4-Methoxybenzyl)-5-bromo-4-methyl-3-nitro-2-pyridone

Product 1

HCID 217064931-(4-Methoxybenzyl)-5-bromo-4-methyl-3-amino-2-pyridoneYield 61.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 1-(4-methoxybenzyl)-5-bromo-4-methyl-3-nitro-2-pyridone (0.23 g, 0.65 mmol) in glacial acetic acid (3 mL) was added a solution of stannous chloride dihydrate (1.0 g) in concentrated HCl (2 mL). After 3.5 hours, the reaction mixture was diluted with water, neutralized with NaHCO3, and extracted with methylene chloride. The organic phase was dried, filtered, and evaporated to give 1-(4-methoxybenzyl)-5-bromo-4-methyl-3-amino-2-pyridone (0.13 g, 0.40 mmol, 61%).

Workup

  1. extractionextracted with methylene chloride
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-d50d134e267746858ac45471d8f700fe
Source dataset
uspto-grants-2000_04
Patent number
US06054470

Reaction notes

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