Ethyl 3-methoxy-4-(3-morpholinopropoxy)-6-nitrobenzoate → Ethyl 3-methoxy-4-(3-morpholinopropoxy)-6-aminobenzoate

HRID 2233238Notes

Reaction equation

HRID 2233238 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([N+:24]([O-])=O)=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]>[Pd].C(O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([NH2:24])=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 1

HCID 11773033Ethyl 3-methoxy-4-(3-morpholinopropoxy)-6-nitrobenzoate

Product 1

HCID 11809903Ethyl 3-methoxy-4-(3-morpholinopropoxy)-6-aminobenzoateYield 100.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of ethyl 3-methoxy-4-(3-morpholinopropoxy)-6-nitrobenzoate (132.2 g, 359 mmol) and 10% palladium on carbon (3.0 g) in a mixture of ethanol (200 ml) and ethyl acetate (2000 ml) was stirred under an atmosphere of hydrogen for 18 hours. Removal of the catalyst by filtration, followed by solvent evaporation in vacuo yielded ethyl 3-methoxy-4-(3-morpholinopropoxy)-6-aminobenzoate (122 g, 100% yield) as a brown oil:

Workup

  1. customRemoval of the catalyst
  2. filtrationby filtration
  3. customfollowed by solvent evaporation in vacuo

Sources & evidence

ORD record
ord-34256ff2d1ba4da4a13d479874053693
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

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