Methyl 3-hydroxy-5-methoxy-4-nitrophenylacetate → Methyl 4-amino-3-hydroxy-5-methoxy-phenylacetate

HRID 1357862Notes

Reaction equation

HRID 1357862 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:5]=[C:6]([O:11][CH3:12])[C:7]=1[N+:8]([O-])=O>C(O)C.[Pd]>[NH2:8][C:7]1[C:6]([O:11][CH3:12])=[CH:5][C:4]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:3][C:2]=1[OH:1]

Participants

4

Reactant 1

HCID 18188097Methyl 3-hydroxy-5-methoxy-4-nitrophenylacetate

Product 1

HCID 18188079Methyl 4-amino-3-hydroxy-5-methoxy-phenylacetateYield 100.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of methyl 3-hydroxy-5-methoxy-4-nitrophenylacetate (0.34 g, Reference Example 11) in ethanol (25 mL) was treated with palladium on charcoal (approximately 0.035 g, 10%) and stirred under a hydrogen atmosphere. After 2 hours the mixture was filtered through a pad of celite and the filtrate was evaporated to give the title compound (0.3 g ) as a brown oil.

Workup

  1. filtrationAfter 2 hours the mixture was filtered through a pad of celite
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-6df3da697a494f0e9ba9556c97cfb797
Source dataset
uspto-grants-2003_07
Patent number
US06593354B2

Reaction notes

Loading…