1-(4-Methoxybenzyl)-5-iodo-4-methyl-3-nitro-2-pyridone → 3-Amino-1-(4-methoxybenzyl)-5-iodo-4-methyl-2-pyridone

HRID 1387280Notes

Reaction equation

HRID 1387280 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[CH:13]=[C:12]([I:14])[C:11]([CH3:15])=[C:10]([N+:16]([O-])=O)[C:9]2=[O:19])=[CH:5][CH:4]=1>C(O)(=O)C.Cl>[NH2:16][C:10]1[C:9](=[O:19])[N:8]([CH2:7][C:6]2[CH:20]=[CH:21][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:13]=[C:12]([I:14])[C:11]=1[CH3:15]

Participants

4

Reactant 1

HCID 217065161-(4-Methoxybenzyl)-5-iodo-4-methyl-3-nitro-2-pyridone

Product 1

HCID 217064763-Amino-1-(4-methoxybenzyl)-5-iodo-4-methyl-2-pyridoneYield 29%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

To a stirred solution of 1-(4-methoxybenzyl)-5-iodo-4-methyl-3-nitro-2-pyridone (1.00 g, 2.5 mmol) in acetic acid (12 mL), cooled on ice, was added a solution of stannous chloride dihydrate (2.85 g, 12.6 mmol) in concentrated HCl (8 mL). After 1 hour the mixture was filtered, and the filtrate was neutralized with solid sodium carbonate (adding water as necessary). The mixture was extracted with methylene chloride, and the organic phase was washed, dried, and evaporated to give 3-amino-1-(4-methoxybenzyl)-5-iodo-4-methyl-2-pyridone (0.265 g, 29%) as an oil.

Workup

  1. filtrationAfter 1 hour the mixture was filtered
  2. extractionThe mixture was extracted with methylene chloride
  3. washthe organic phase was washed
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-d39fdad5c40b481891c39949eed13349
Source dataset
uspto-grants-2001_07
Patent number
US06268365B1

Reaction notes

Loading…