Ethyl Acetate → methyl 2-amino-3-(tetrahydro-2H-pyran-4-yloxy)benzoate

HRID 1672462Notes

Reaction equation

HRID 1672462 reaction equation
[N+:1]([C:4]1[C:13]([O:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])([O-])=O.C(OCC)(=O)C>CO.[Ni]>[NH2:1][C:4]1[C:13]([O:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 58082227methyl 2-nitro-3-(tetrahydro-2H-pyran-4-yloxy)benzoate

Product 1

HCID 58082434methyl 2-amino-3-(tetrahydro-2H-pyran-4-yloxy)benzoateYield 72%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 2-nitro-3-(tetrahydro-2H-pyran-4-yloxy)benzoate (1.3 g, 4.8 mmol) and Raney Ni (0.5 g) in MeOH (30 mL) was stirred under 1 atm of H2 at room temperature for 24 h. TLC (petroleum ether:ethyl acetate=1:1) showed the reaction was complete. The mixture was filtered, the filtrate was concentrated in vacuo. The residue was purified by chromatography (petroleum ether:ethyl acetate=20:1) to give the title compound (0.8 g, 72%) as a colorless oil.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by chromatography (petroleum ether:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-58d5e16a938c4bf4822312954a20d420
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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