Methyl 3-methyl-4-(2-methoxy-5-nitrophenoxy)butyrate → Methyl 3-methyl-4-(2-methoxy-5-aminophenoxy)butyrate

HRID 2305630Notes

Reaction equation

HRID 2305630 reaction equation
[CH3:1][CH:2]([CH2:8][O:9][C:10]1[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:11]=1[O:19][CH3:20])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[H][H]>CO.[Pd]>[CH3:1][CH:2]([CH2:8][O:9][C:10]1[CH:15]=[C:14]([NH2:16])[CH:13]=[CH:12][C:11]=1[O:19][CH3:20])[CH2:3][C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 18433387Methyl 3-methyl-4-(2-methoxy-5-nitrophenoxy)butyrateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 11322746Methyl 3-methyl-4-(2-methoxy-5-aminophenoxy)butyrate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

At ambient temperature a rapidly stirred solution of methyl 3-methyl-4-(2-methoxy-5-nitrophenoxy)butyrate(400 mg) in methanol (20 mL) containing 10% palladium on carbon (40 mg) was exposed to an atmosphere of hydrogen. When uptake of hydrogen had ceased the solution was filtered and the filter cake washed with methanol. The combined filtrates were evaporated to dryness under reduced pressure, to give methyl 3-methyl-4-(2-methoxy-5-aminophenoxy)butyrate as an oil. (317 mg) m/Z 254(M+H).

Workup

  1. filtrationwas filtered
  2. washthe filter cake washed with methanol
  3. customThe combined filtrates were evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-3f77f4683d644ee1a3028b3cc4762386
Source dataset
uspto-grants-2002_08
Patent number
US06441012B1

Reaction notes

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