2-Nitro-5-(3-oxo-morpholin-4-yl)-benzonitrile → 2-Amino-5-(3-oxo-morpholin-4-YL)-benzonitrile

HRID 2244683Notes

Reaction equation

HRID 2244683 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C:13]2=[O:18])=[CH:8][C:5]=1[C:6]#[N:7])([O-])=O>C1COCC1.[Pd]>[NH2:1][C:4]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C:13]2=[O:18])=[CH:8][C:5]=1[C:6]#[N:7]

Participants

4

Reactant 1

HCID 588264662-Nitro-5-(3-oxo-morpholin-4-yl)-benzonitrile

Product 1

HCID 534164642-Amino-5-(3-oxo-morpholin-4-YL)-benzonitrileYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-nitro-5-(3-oxo-morpholin-4-yl)-benzonitrile (1.1 g) in THF (80 ml) was hydrogenated at 1 atm in the presence of Pd/C 10% (350 mg) at room temperature. The reaction mixture was filtered through decalite and precipitated (AcOEt/heptane) to yield 2-amino-5-(3-oxo-morpholin-4-yl)-benzonitrile as a white solid (580 mg). MS: 218.4 ([M+H]+).

Workup

  1. filtrationThe reaction mixture was filtered through decalite
  2. customprecipitated (AcOEt/heptane)

Sources & evidence

ORD record
ord-435057e56a614cf9996b8dedd617d7d3
Source dataset
uspto-grants-2010_03
Patent number
US07678917B2

Reaction notes

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