Methyl 4-cyclobutyl-3-nitrobenzoate → Methyl 3-amino-4-cyclobutylbenzoate

HRID 541448Notes

Reaction equation

HRID 541448 reaction equation
[CH:1]1([C:5]2[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=2[N+:15]([O-])=O)[CH2:4][CH2:3][CH2:2]1>CO>[NH2:15][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:5]=1[CH:1]1[CH2:4][CH2:3][CH2:2]1)[C:9]([O:11][CH3:12])=[O:10]

Participants

3

Reactant 1

HCID 68288364Methyl 4-cyclobutyl-3-nitrobenzoate2×

Product 1

HCID 68288285Methyl 3-amino-4-cyclobutylbenzoateYield 73.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

A flask containing a solution of methyl 4-cyclobutyl-3-nitrobenzoate (compound 443.1, 2.50 g, 10.6 mmol, 1.00 equiv) in methanol (30 mL) was purged with nitrogen. Palladium on carbon (10%, 60% water, 1.2 g) was added and the flask was carefully purged further with nitrogen. The atmosphere was then changed to hydrogen and the mixture was stirred overnight at 20° C. After purging the system with nitrogen, the solids were then removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified using silica gel column chromatography with ethyl acetate/petroleum ether (1:5) as eluent to yield 1.60 g (73%) of the title compound as a white solid.

Workup

  1. customwas purged with nitrogen
  2. additionPalladium on carbon (10%, 60% water, 1.2 g) was added
  3. customthe flask was carefully purged further with nitrogen
  4. customAfter purging the system with nitrogen
  5. customthe solids were then removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified

Sources & evidence

ORD record
ord-7284a7639fcb48af89f8e872ae26662f
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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