Methyl (4-nitrophenoxy)acetate → Methyl(4-aminophenoxy)acetate

HRID 1601814Notes

Reaction equation

HRID 1601814 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=1)([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 700522Methyl (4-nitrophenoxy)acetate

Product 1

HCID 6422115Methyl(4-aminophenoxy)acetateYield 97.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A procedure similar to that described in Example 6 was repeated, except that 30.8 g of methyl 4-nitrophenoxyacetate (prepared as described in Preparation 36), 5.0 g of 10% w/w palladium-on-charcoal and 500 ml of methanol were used, to give 25.8 g of the title compound having Rf=0.79 (on silica gel thin layer chromatography using ethyl acetate as the developing solvent).

Sources & evidence

ORD record
ord-fc875c7539e4400387fbeb39f8e53cfe
Source dataset
uspto-grants-1999_11
Patent number
US05977365

Reaction notes

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